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Home > Encyclopedia > Z-TRANS-4-HYDROXY-L-PROLINOL

Z-TRANS-4-HYDROXY-L-PROLINOL

Z-TRANS-4-HYDROXY-L-PROLINOL structure

Z-TRANS-4-HYDROXY-L-PROLINOL 

structure
  • CAS No:

    95687-41-5

  • Formula:

    C13H17NO4

  • Chemical Name:

    Z-TRANS-4-HYDROXY-L-PROLINOL

  • Synonyms:

    CBZ-TRANS-4-HYDROXY-L-PROLINOL;(2S,4R)4-Hydroxy-2-(hydroxymethyl)pyrrolidine, N-CBZ protected;1-CBZ-TRANS-4-HYDROXY-L-PROLINOL;N-CBZ-TRANS-4-HYDROXY-L-PROLINOL;TRANS-N-CBZ-4-HYDROXY-L-PROLINOL;Trans-N-benzyloxycarbonyl-4-hydroxy-2-hydroxymethylpyrrolidine;Z-Hyp-Ol;Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

  • Categories:

    Biochemical Engineering  >  Amino Acids and Derivatives

Z-TRANS-4-HYDROXY-L-PROLINOL Basic Attributes

251.27838

251.115753

DTXSID00566696

2933990090

Characteristics

70

0.5

1.3±0.1 g/cm3

240 °C(lit.)

>230 °F

1.589

Safety Information

IRRITANT

NONH for all modes of transport

3

Xi

Z-TRANS-4-HYDROXY-L-PROLINOL Use and Manufacturing

Benzyl (4R)-hydroxy-(2S)-hydroxymethylpyrrolidine-1-carboxylate (2S, 4R)-N-LBeLzyloxvcarbonvo-2-hydroxymethyl-4-hydroxvpvrrolidine (6); To a stirred, cold (0 °C) solution of intermediate (5) (58.4 g, 0.208 mol) in THF (400 mL) was added LiBH4 (3.5 g, 0.16 mol) portion-wise. The reaction mixture was stirred for 30 min at (0-5 °C) then for 4 h at room temperature. At this time, TLC (silica gel plates developed in EtOAc) showed just a trace of starting material. The thick reaction mixture was diluted in succession with H20 (250 mL) and 2 M HC1 (277 mL), and then concentrated in vacuo to remove THF. The resulting aqueous concentrate was extracted with EtOAc (4 x 175 mL). Combined EtOAc extracts were washed with brine (2 x 200 mL), dried over MgS04, and then concentrated in vacuo to give intermediate (5) as an oil (51.9 g, 99percent). Additional reactions were carried out to give a total of 227 g of product suitable for further transformation. In later preparations the more convenient commercial solution of LiBH4 in THF was usedEXAMPLE 22

Computed Properties

Molecular Weight:251.28
XLogP3:0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:251.11575802
Monoisotopic Mass:251.11575802
Topological Polar Surface Area:70
Heavy Atom Count:18
Complexity:278
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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