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

Base Information

Chemical Name:(Z)-(R)-7-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-6-en-2-ol
CAS No.:912351-88-3
Molecular Formula:C₂₀H₃₀O₄
Molecular Weight:334.456
Hs Code.:

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

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Chemical Property of (Z)-(R)-7-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-6-en-2-ol

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Technology Process of (Z)-(R)-7-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-6-en-2-ol

There total 9 articles about (Z)-(R)-7-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-6-en-2-ol 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: 89.0%

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

: 912351-88-3
(Z)-(R)-7-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-6-en-2-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1h;
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

: 912351-88-3
(Z)-(R)-7-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-6-en-2-ol

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 89 percent / LAH / tetrahydrofuran / 1 h / 0 °C

With lithium aluminium tetrahydride; potassium tert-butylate; (S,S)-(salen)manganese; In tetrahydrofuran; 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

: 912351-88-3
(Z)-(R)-7-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-6-en-2-ol

Guidance literature:: Multi-step reaction with 4 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

4: 89 percent / LAH / tetrahydrofuran / 1 h / 0 °C

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