(R)-[3,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-[(1aR,3aS,5S,7aS,7bR)-5-(tert-butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl]-methanol

Base Information

Chemical Name:(R)-[3,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-[(1aR,3aS,5S,7aS,7bR)-5-(tert-butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl]-methanol
CAS No.:393803-75-3
Molecular Formula:C₄₈H₇₂O₆Si₂
Molecular Weight:801.267
Hs Code.:

(R)-[3,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-[(1aR,3aS,5S,7aS,7bR)-5-(tert-butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl]-methanol

Synonyms:(R)-[3,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-[(1aR,3aS,5S,7aS,7bR)-5-(tert-butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl]-methanol

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Chemical Property of (R)-[3,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-[(1aR,3aS,5S,7aS,7bR)-5-(tert-butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl]-methanol

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Technology Process of (R)-[3,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-[(1aR,3aS,5S,7aS,7bR)-5-(tert-butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl]-methanol

There total 11 articles about (R)-[3,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-[(1aR,3aS,5S,7aS,7bR)-5-(tert-butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl]-methanol 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: 48.0%

: 393803-41-3
(1aR,3aS,5S,7aS,7bS)-5-(tert-Butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalene-7b-carbaldehyde

: 393803-57-1
1,2-dibenzyloxy-4-bromo-5-tert-butyldimethylsilyloxy-3-methylbenzene

: 393803-75-3
(R)-[3,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-[(1aR,3aS,5S,7aS,7bR)-5-(tert-butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl]-methanol

: 393803-61-7
(S)-[3,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-[(1aR,3aS,5S,7aS,7bR)-5-(tert-butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl]-methanol

Guidance literature:: 1,2-dibenzyloxy-4-bromo-5-tert-butyldimethylsilyloxy-3-methylbenzene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 1h;

(1aR,3aS,5S,7aS,7bS)-5-(tert-Butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalene-7b-carbaldehyde; In diethyl ether; pentane; at -78 ℃; for 0.5h; Further stages.;
DOI:10.1021/ol016960n

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 393803-75-3
(R)-[3,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-[(1aR,3aS,5S,7aS,7bR)-5-(tert-butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl]-methanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 86 percent / pyridine / 1 h / 0 °C

2.1: 70 percent / Dibal-H / toluene / 0.5 h / -78 °C

3.1: t-BuLi / diethyl ether; pentane / 1 h / -78 °C

3.2: 15 percent / diethyl ether; pentane / 0.5 h / -78 °C

With pyridine; tert.-butyl lithium; diisobutylaluminium hydride; In diethyl ether; toluene; pentane;
DOI:10.1021/ol016960n

Reference yield:

: 114626-74-3
(1aR,3aS,5S,7aS,7bS)-5-Acetoxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalene-7b-carboxylic acid methyl ester

: 393803-75-3
(R)-[3,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-phenyl]-[(1aR,3aS,5S,7aS,7bR)-5-(tert-butyl-dimethyl-silanyloxy)-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl]-methanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 286 mg / NaOMe / methanol / 22 h / 20 °C

2.1: 86 percent / pyridine / 1 h / 0 °C

3.1: 70 percent / Dibal-H / toluene / 0.5 h / -78 °C

4.1: t-BuLi / diethyl ether; pentane / 1 h / -78 °C

4.2: 15 percent / diethyl ether; pentane / 0.5 h / -78 °C

With pyridine; tert.-butyl lithium; sodium methylate; diisobutylaluminium hydride; In methanol; diethyl ether; toluene; pentane;
DOI:10.1021/ol016960n