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Hoffer's chlorosugar

Hoffer's chlorosugar structure

CAS No:
4330-21-6
Formula:
C21H21ClO5
Chemical Name:
Hoffer's chlorosugar
Synonyms:
α-D-erythro-Pentofuranosyl chloride,2-deoxy-,3,5-bis(4-methylbenzoate);D-erythro-Pentofuranosyl chloride,2-deoxy-,di-p-toluate,α-;α-D-erythro-Pentofuranosyl chloride,2-deoxy-,bis(4-methylbenzoate);p-Toluic acid,diester with 2-deoxy-α-D-erythro-pentofuranosyl chloride;3,5-Di-O-p-toluyl-2-deoxy-α-D-ribofuranosyl chloride;1-Chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose;2-Deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride;NSC 148837;Hoffer's chlorosugar;Hoffer's α-chlorosugar;1-Chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-ribose;Hoffer's sugar;(2R,3S,5R)-5-Chloro-2-[[(4-methylbenzoyl)oxy]methyl]tetrahydrofuran-3-yl] 4-methylbenzoate;3,5-Di-O-toluoyl-α-1-chloro-2-deoxy-D-ribofuranose;1-Chloro-2-deoxy-3,5-di-O-toluoyl-a-D-ribofuranose;1-α-Chloro-3,5-ditoluoyl-2-deoxy-D-ribose;104748-60-9;793674-18-7;1044273-25-7;1088901-08-9
Categories:
Biochemical Engineering > Saccharides

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Description

White solid

Hoffer's chlorosugar Basic Attributes

Molecular Weight：

388.84

Exact Mass：

388.84

EC Number：

224-367-3

NSC Number：

148837

HScode：

29321900

Characteristics

PSA：

61.8

XLogP3：

4.48360

Density：

1.2±0.1 g/cm3

Melting Point：

117-119 °C

Boiling Point：

518.4°C at 760 mmHg

Flash Point：

158.9±28.8 °C

Refractive Index：

1.578

Storage Conditions：

−20°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36

Marks：

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 42 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hoffer's chlorosugar Use and Manufacturing

The pentofuranose 9(50.0 g, 0.13 mol) was dissolved in glacial acetic acid (150 mL) by stirring at rt for 20 min under an argon atmosphere. The solution was cooled to 10-15 °C and 4M HCl in dioxane (150 mL, 0.6 mol) was added dropwise (5 min). The pale, straw-coloured solution was seeded with a small amount of compound 10 and stirred briefly until a precipitate started to form. The stirring was stopped and the reaction mixture stood (40min) with cooling (ice/water). The resultant white slurry was broken up by swirling the flask and filtered rapidly. The filter cake was packed down, washed with cold ether (3 x 30 mL) and dried under high vacuum to give compound 10 (34.1 g, 67percent) as a white solid. Spectroscopic and analytical data were in agreement with the data published previously.22 Rf 0.58 (EtOAc-Hexane 1:2). IR (cm-1): 3030, 2951, 1708, 1276, 1178, 1099, 755. 1HNMR (250.1 MHz, CDCl3): d 2.41 (s, 3H, CH3), 2.42 (s, 3H, CH3), 2.74 (m, 1H, 2-CH), 2.84 (m, 1H, 2-CH), 4.61 (dd, J 12.1, 4.1 Hz, 1H, 5-CH), 4.66 (dd, J 12.1 Hz, 4.1 Hz, 1H, 5-CH), 4.85 (m, 1H, 4-CH), 5.58 (m, 1H, 3-CH), 6.47 (d, J4.2 Hz, 1H, 1-CH), 7.24 (d, J 8.3 Hz, 2H, 3, 5-tol-CH), 7.26 (d, J 8.3 Hz, 2H, 3, 5-tol-CH), 7.90 (d, J 8.3 Hz, 2H, 2, 6-tol-CH), 7.99 (d, J 8.3 Hz, 2H, 2, 6-tol-CH). 13C NMR (62.9 MHz, CDCl3): d 21.70 (CH3), 21.71 (CH3), 44.54 (2-CH2), 63.51 (5-CH2), 73.56 (4-CH), 84.71 (3-CH), 95.3 (1-CH), 126.66 (C), 126.72 (C), 129.19 (CH), 129.21 (CH), 129.63(CH), 129.88 (CH), 144.07 (C), 144.30 (C), 166.07 (CO), 166.41 (CO). MS (EI): m/z (percent) 353 (M-. – Cl, 1), 252 (1), 216 (32), 136 (38), 119 (100), 91 (78), 81 (100), 65 (28), 53 (25), 39 (19). Anal. Calcd for C21H22ClO5: C, 64.8; H, 5.41. Found: C, 64.4; H, 5.39.

Computed Properties

Molecular Weight:388.8
XLogP3:4.9
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:388.1077515
Monoisotopic Mass:388.1077515
Topological Polar Surface Area:61.8
Heavy Atom Count:27
Complexity:509
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate)

CAS No.: 4330-21-6

Grade: industrial Grade

Content: 98%

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Shaanxi Dideu Medichem Co. Ltd Contact Supplier

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2-Deoxy-alpha-D-erythropentofuranosyl chloride 3,5-bis(4-methylbenzoate)

CAS No.: 4330-21-6

Grade: Industrial Grade

Content: 99%

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Guide of Hoffer's chlorosugar

Description
Basic Attributes
Characteristics
Safety Information
Use and Manufacturing
Computed Properties
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Hoffer's chlorosugar

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