tert-butyl (1R,2S,3S,6R,7S,4'S)-6-benzyloxy-7-ethenyl-3-hydroxy-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-bicyclo[4.1.0]heptane-1-carboxylate

Base Information

Chemical Name:tert-butyl (1R,2S,3S,6R,7S,4'S)-6-benzyloxy-7-ethenyl-3-hydroxy-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-bicyclo[4.1.0]heptane-1-carboxylate
CAS No.:196614-83-2
Molecular Formula:C₂₆H₃₆O₆
Molecular Weight:444.568
Hs Code.:

Synonyms:tert-butyl (1R,2S,3S,6R,7S,4'S)-6-benzyloxy-7-ethenyl-3-hydroxy-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-bicyclo[4.1.0]heptane-1-carboxylate

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Chemical Property of tert-butyl (1R,2S,3S,6R,7S,4'S)-6-benzyloxy-7-ethenyl-3-hydroxy-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-bicyclo[4.1.0]heptane-1-carboxylate

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Technology Process of tert-butyl (1R,2S,3S,6R,7S,4'S)-6-benzyloxy-7-ethenyl-3-hydroxy-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-bicyclo[4.1.0]heptane-1-carboxylate

There total 2 articles about tert-butyl (1R,2S,3S,6R,7S,4'S)-6-benzyloxy-7-ethenyl-3-hydroxy-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-bicyclo[4.1.0]heptane-1-carboxylate 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: 65.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: tert-butyl (1S,3S*,4S,5S,6R,9S,4'S)-6-benzyloxy-3-hydroxy-9-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-2-oxatricyclo[3.3.1.0^4.6]nonane-5-carboxylate

: 196614-83-2
tert-butyl (1R,2S,3S,6R,7S,4'S)-6-benzyloxy-7-ethenyl-3-hydroxy-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-bicyclo[4.1.0]heptane-1-carboxylate

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; Ambient temperature;
DOI:10.1055/s-1997-1273

Reference yield:

: 185840-31-7
(1S,2S,5S,8R,9S)-8-Benzyloxy-9-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-oxo-4-oxa-tricyclo[3.3.1.0^2,8]nonane-1-carboxylic acid tert-butyl ester

: 196614-83-2
tert-butyl (1R,2S,3S,6R,7S,4'S)-6-benzyloxy-7-ethenyl-3-hydroxy-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-bicyclo[4.1.0]heptane-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / DIBALH / tetrahydrofuran; toluene; diethyl ether / 2 h / -70 - -40 °C

2: 65 percent / t-BuOK / tetrahydrofuran / Ambient temperature

With potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1055/s-1997-1273