(1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one

Base Information

Chemical Name:(1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one
CAS No.:249890-38-8
Molecular Formula:C₁₇H₁₆O₅
Molecular Weight:300.311
Hs Code.:

Synonyms:(1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one

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Chemical Property of (1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one

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Technology Process of (1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one

There total 5 articles about (1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one 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%

: 15097-38-8
(carbobenzyloxymethylene)triphenylphosphorane

: (1aS,1bS,4aS,5aR)-3-Oxo-hexahydro-1,4-dioxa-cyclopropa[a]pentalene-1a-carbaldehyde

: 249890-38-8
(1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one

Guidance literature:: In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo990906r

Reference yield:

: 62158-44-5
(1S,5R)-6-hydroxymethyl-2-oxabicyclo[3.3.0]oct-6-en-3-one

: 249890-38-8
(1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: 75 percent / Ti(i-PrO)4; (-)-D-diethyl tartrate; t-BuOOH / CH₂Cl₂ / 3 h / -23 °C

2: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.83 h / -78 - 0 °C

3: 89 percent / CH₂Cl₂ / 2 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2S,3S)-tartrate; dimethyl sulfoxide; triethylamine; In dichloromethane; 1: Sharpless asymmetric epoxidation / 2: Swern oxidation / 3: Wittig reaction;
DOI:10.1021/jo990906r

Reference yield:

: 51260-12-9
(1S,5S)-3-oxo-2-oxabicyclo<3.3.0>oct-6-en-6-carbaldehyde

: 249890-38-8
(1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / NaBH₄; CeCl₃*7H₂O / CH₂Cl₂; methanol / 1.5 h / -78 °C

2: 75 percent / Ti(i-PrO)4; (-)-D-diethyl tartrate; t-BuOOH / CH₂Cl₂ / 3 h / -23 °C

3: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.83 h / -78 - 0 °C

4: 89 percent / CH₂Cl₂ / 2 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; diethyl (2S,3S)-tartrate; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; 1: Luche readuction / 2: Sharpless asymmetric epoxidation / 3: Swern oxidation / 4: Wittig reaction;
DOI:10.1021/jo990906r