(3R,4S,5S)-3,4,5-Tris-benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-7-oxa-bicyclo[4.1.0]heptan-2-ol

Base Information

Chemical Name:(3R,4S,5S)-3,4,5-Tris-benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-7-oxa-bicyclo[4.1.0]heptan-2-ol
CAS No.:305383-48-6
Molecular Formula:C₃₃H₃₈O₇
Molecular Weight:546.661
Hs Code.:

Synonyms:(3R,4S,5S)-3,4,5-Tris-benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-7-oxa-bicyclo[4.1.0]heptan-2-ol

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Chemical Property of (3R,4S,5S)-3,4,5-Tris-benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-7-oxa-bicyclo[4.1.0]heptan-2-ol

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Technology Process of (3R,4S,5S)-3,4,5-Tris-benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-7-oxa-bicyclo[4.1.0]heptan-2-ol

There total 1 articles about (3R,4S,5S)-3,4,5-Tris-benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-7-oxa-bicyclo[4.1.0]heptan-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:

: 304672-03-5
(4R,5S,6S)-4,5,6-Tris-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-cyclohex-2-enone

: 305383-48-6
(3R,4S,5S)-3,4,5-Tris-benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-7-oxa-bicyclo[4.1.0]heptan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 65 percent / 30 percent H₂O₂; K₂CO₃ / H₂O; tetrahydrofuran / 6 h / 0 °C

2: 93 percent / NaBH₄ / methanol / 0.25 h / -40 °C

With sodium tetrahydroborate; dihydrogen peroxide; potassium carbonate; In tetrahydrofuran; methanol; water;
DOI:10.3987/com-00-8987

Reference yield: 98.0%

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 305383-48-6
(3R,4S,5S)-3,4,5-Tris-benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-7-oxa-bicyclo[4.1.0]heptan-2-ol

: 305383-49-7
Imidazole-1-carbothioic acid O-[(3R,4S,5S)-3,4,5-tris-benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-7-oxa-bicyclo[4.1.0]hept-2-yl] ester

Guidance literature:: In benzene; at 80 ℃; for 12h;
DOI:10.3987/com-00-8987

Reference yield:

: 305383-48-6
(3R,4S,5S)-3,4,5-Tris-benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-7-oxa-bicyclo[4.1.0]heptan-2-ol

: (4R,5S,6S)-4,5,6-Tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / benzene / 12 h / 80 °C

2: 30 percent / Bu₃SnH; AIBN / benzene / 4 h / 80 °C

3: 87 percent / MnO₂ / CH₂Cl₂ / 45 °C

With manganese(IV) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In dichloromethane; benzene;
DOI:10.3987/com-00-8987