Acetic acid (Z)-(R)-6-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-hex-5-enyl ester

Base Information

Chemical Name:Acetic acid (Z)-(R)-6-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-hex-5-enyl ester
CAS No.:912351-89-4
Molecular Formula:C₂₂H₃₂O₅
Molecular Weight:376.493
Hs Code.:

Synonyms:Acetic acid (Z)-(R)-6-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-hex-5-enyl ester

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Chemical Property of Acetic acid (Z)-(R)-6-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-hex-5-enyl ester

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Technology Process of Acetic acid (Z)-(R)-6-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-hex-5-enyl ester

There total 10 articles about Acetic acid (Z)-(R)-6-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-hex-5-enyl ester 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: 92.0%

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

: 75-36-5
acetyl chloride

: 912351-89-4
Acetic acid (Z)-(R)-6-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-hex-5-enyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2h;
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

: 912351-89-4
Acetic acid (Z)-(R)-6-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-hex-5-enyl ester

Guidance literature:: Multi-step reaction with 4 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

4: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 °C

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

: 912351-89-4
Acetic acid (Z)-(R)-6-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-hex-5-enyl ester

Guidance literature:: Multi-step reaction with 5 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

5: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 °C

With dmap; 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