Malic Acid → Methyl (6S)-6,8-dihydroxyoctanoate

HRID 260913Notes

Reaction equation

HRID 260913 reaction equation
[C:1]([OH:9])(=[O:8])[CH:2]([CH2:4][C:5](O)=O)O.C1(C[O:17][CH2:18][CH2:19][C@@H:20]([OH:23])[CH2:21]O)C=CC=CC=1.[C:24]1(COCC[C@@H]2CO2)C=CC=CC=1.OC(CCOCC1C=CC=CC=1)CCCC=C>>[OH:23][C@H:20]([CH2:19][CH2:18][OH:17])[CH2:21][CH2:5][CH2:4][CH2:2][C:1]([O:9][CH3:24])=[O:8]

Participants

5

Reactant 4

HCID 525Malic AcidHCID 10910454(R)-4-Benzyloxy-1,2-butanediolHCID 11789783(2R)-2-[2-(Phenylmethoxy)ethyl]oxiraneHCID 137170876-Hydroxy-8-(phenylmethoxy)-l-octene

Product 1

HCID 10899438Methyl (6S)-6,8-dihydroxyoctanoate

Procedure

Chem. Soc. Perkin Trans. I (1988) 9 describes the preparation thereof from the malic acid derivative (S)-4-phenylmethoxy-1,2-butanediol by a multistage reaction sequence with the intermediates (R)-4-phenylmethoxy-1,2-butanediol, (R)-(2-phenylmethoxyethyl)oxirane, 6-hydroxy-8-(phenylmethoxy)-l-octene to give methyl (6S)-6,8-dihydroxyoctanoate.

Workup

  1. customthe preparation

Sources & evidence

ORD record
ord-d36701c2602f45c7a4ffedd68d223a48
Source dataset
uspto-grants-1996_06
Patent number
US05530143

Reaction notes

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