(4S,5S)-4-Benzyloxymethyl-2,2-dimethyl-5-((Z)-(S)-5-oxiranyl-pent-1-enyl)-[1,3]dioxolane

Base Information

Chemical Name:(4S,5S)-4-Benzyloxymethyl-2,2-dimethyl-5-((Z)-(S)-5-oxiranyl-pent-1-enyl)-[1,3]dioxolane
CAS No.:912351-86-1
Molecular Formula:C₂₀H₂₈O₄
Molecular Weight:332.44
Hs Code.:

Synonyms:(4S,5S)-4-Benzyloxymethyl-2,2-dimethyl-5-((Z)-(S)-5-oxiranyl-pent-1-enyl)-[1,3]dioxolane

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Chemical Property of (4S,5S)-4-Benzyloxymethyl-2,2-dimethyl-5-((Z)-(S)-5-oxiranyl-pent-1-enyl)-[1,3]dioxolane

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Technology Process of (4S,5S)-4-Benzyloxymethyl-2,2-dimethyl-5-((Z)-(S)-5-oxiranyl-pent-1-enyl)-[1,3]dioxolane

There total 8 articles about (4S,5S)-4-Benzyloxymethyl-2,2-dimethyl-5-((Z)-(S)-5-oxiranyl-pent-1-enyl)-[1,3]dioxolane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 42.0%

: 912351-85-0
(4S,5S)-4-Benzyloxymethyl-2,2-dimethyl-5-((Z)-5-oxiranyl-pent-1-enyl)-[1,3]dioxolane

: 912351-86-1
(4S,5S)-4-Benzyloxymethyl-2,2-dimethyl-5-((Z)-(S)-5-oxiranyl-pent-1-enyl)-[1,3]dioxolane

: (Z)-(R)-7-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-6-ene-1,2-diol

Guidance literature:: (S,S)-(salen)manganese; In water; at 20 ℃; for 12h;
DOI:10.1016/j.tetlet.2006.07.043

Reference yield:

: 912351-84-9
(Z)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hex-5-enal

: 912351-86-1
(4S,5S)-4-Benzyloxymethyl-2,2-dimethyl-5-((Z)-(S)-5-oxiranyl-pent-1-enyl)-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 2 steps

1: 53 percent / t-BuOK / dimethylsulfoxide / 1 h / 0 °C

2: 40 percent / S,S-Jacobsen catalyst / H₂O / 12 h / 20 °C

With potassium tert-butylate; (S,S)-(salen)manganese; In water; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2006.07.043

Reference yield:

: 912351-83-8
(Z)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hex-5-en-1-ol

: 912351-86-1
(4S,5S)-4-Benzyloxymethyl-2,2-dimethyl-5-((Z)-(S)-5-oxiranyl-pent-1-enyl)-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂ / 2 h / -78 °C

2: 53 percent / t-BuOK / dimethylsulfoxide / 1 h / 0 °C

3: 40 percent / S,S-Jacobsen catalyst / H₂O / 12 h / 20 °C

With oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; triethylamine; (S,S)-(salen)manganese; In dichloromethane; water; dimethyl sulfoxide; 1: Swern oxidation;
DOI:10.1016/j.tetlet.2006.07.043