((1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octan-6-yl)methanol

Base Information

Chemical Name:((1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octan-6-yl)methanol
CAS No.:1352577-38-8
Molecular Formula:C₃₃H₅₂O₄Si₂
Molecular Weight:568.944
Hs Code.:

Synonyms:((1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octan-6-yl)methanol

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Chemical Property of ((1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octan-6-yl)methanol

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Technology Process of ((1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octan-6-yl)methanol

There total 9 articles about ((1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octan-6-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: 77.0%

: 1352577-49-1
2-((1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-(hydroxymethyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethanol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1352577-38-8
((1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octan-6-yl)methanol

Guidance literature:: With pyridine; dmap; at 23 ℃; for 21h; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.079

Reference yield:

: 1352577-48-0
(1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-hydroxyethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carboxylic acid

: 1352577-38-8
((1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octan-6-yl)methanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16.25 h / 23 - 35 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 20 h / 75 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / diethyl ether / 42 h / -40 °C / Inert atmosphere

3.2: 1.5 h / -40 - 23 °C / Inert atmosphere

4.1: pyridine; dmap / 21 h / 23 °C / Inert atmosphere

With pyridine; dmap; lithium aluminium tetrahydride; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In diethyl ether; dichloromethane; benzene;
DOI:10.1016/j.tet.2011.09.079

Reference yield:

: 1352577-37-7
(1S,2R,7S,8S,9R)-9-(tert-butyldimethylsilyloxy)-1-methyl-4,12-dioxa-tricyclo[6.3.1.0(2,7)]dodecan-3-one

: 1352577-38-8
((1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octan-6-yl)methanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 42 h / -40 °C / Inert atmosphere

1.2: 1.5 h / -40 - 23 °C / Inert atmosphere

2.1: pyridine; dmap / 21 h / 23 °C / Inert atmosphere

With pyridine; dmap; lithium aluminium tetrahydride; In diethyl ether;
DOI:10.1016/j.tet.2011.09.079