(2S,5R,6R)-2-benzyloxy-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-3-heptanone

Base Information

Chemical Name:(2S,5R,6R)-2-benzyloxy-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-3-heptanone
CAS No.:1415122-24-5
Molecular Formula:C₃₀H₃₈O₄Si
Molecular Weight:490.715
Hs Code.:

Synonyms:(2S,5R,6R)-2-benzyloxy-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-3-heptanone

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Chemical Property of (2S,5R,6R)-2-benzyloxy-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-3-heptanone

Chemical Property:

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Technology Process of (2S,5R,6R)-2-benzyloxy-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-3-heptanone

There total 2 articles about (2S,5R,6R)-2-benzyloxy-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-3-heptanone 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:

: 97203-22-0,98168-70-8
(-)-(S)-3-(phenylmethoxy)-2-butanone

: 167468-64-6
(2R)-2-(tert-butyldiphenylsiloxy)propanal

: 1415122-23-4
(2S,5S,6R)-2-benzyloxy-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-3-heptanone

: 1415122-24-5
(2S,5R,6R)-2-benzyloxy-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-3-heptanone

Guidance literature:: (-)-(S)-3-(phenylmethoxy)-2-butanone; With titanium(IV) trichloride isopropoxide; In dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

(2R)-2-(tert-butyldiphenylsiloxy)propanal; In dichloromethane; at -78 ℃; for 0.5h; Overall yield = 79 %; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2012.09.096 DOI:10.1016/j.tet.2012.09.096

Reference yield:

: 122151-32-0
(S)-2-(benzyloxy)-1-(pyrrolidin-1-yl)propan-1-one

: 1415122-23-4
(2S,5S,6R)-2-benzyloxy-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-3-heptanone

: 1415122-24-5
(2S,5R,6R)-2-benzyloxy-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-3-heptanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: diethyl ether; tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

2.1: titanium(IV) trichloride isopropoxide / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

2.3: 0.5 h / -78 °C / Inert atmosphere

With titanium(IV) trichloride isopropoxide; In tetrahydrofuran; diethyl ether; dichloromethane; 2.3: |Aldol Addition;
DOI:10.1016/j.tet.2012.09.096 DOI:10.1016/j.tet.2012.09.096