(1S,3R,4R,5R)-3-benzyloxy-1,4-bis(tert-butyldimethylsilyloxy)cyclohexane-1,5-carbolactone

Base Information

Chemical Name:(1S,3R,4R,5R)-3-benzyloxy-1,4-bis(tert-butyldimethylsilyloxy)cyclohexane-1,5-carbolactone
CAS No.:862791-08-0
Molecular Formula:C₂₆H₄₄O₅Si₂
Molecular Weight:492.803
Hs Code.:

Synonyms:(1S,3R,4R,5R)-3-benzyloxy-1,4-bis(tert-butyldimethylsilyloxy)cyclohexane-1,5-carbolactone

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Chemical Property of (1S,3R,4R,5R)-3-benzyloxy-1,4-bis(tert-butyldimethylsilyloxy)cyclohexane-1,5-carbolactone

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Technology Process of (1S,3R,4R,5R)-3-benzyloxy-1,4-bis(tert-butyldimethylsilyloxy)cyclohexane-1,5-carbolactone

There total 2 articles about (1S,3R,4R,5R)-3-benzyloxy-1,4-bis(tert-butyldimethylsilyloxy)cyclohexane-1,5-carbolactone 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: 97.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 185810-83-7
(1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-carbolactone

: 862791-08-0
(1S,3R,4R,5R)-3-benzyloxy-1,4-bis(tert-butyldimethylsilyloxy)cyclohexane-1,5-carbolactone

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/jm0501836

Reference yield: 97.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 665-27-0
1,5-quinide

: 862791-08-0
(1S,3R,4R,5R)-3-benzyloxy-1,4-bis(tert-butyldimethylsilyloxy)cyclohexane-1,5-carbolactone

Guidance literature:: With pyridine; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere;

Reference yield:

: 862791-08-0
(1S,3R,4R,5R)-3-benzyloxy-1,4-bis(tert-butyldimethylsilyloxy)cyclohexane-1,5-carbolactone

: 862791-50-2
3-[(1R,4R,5R)-1,4-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-en-3-yl]-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / H₂ / Pd(OH)2/C / methanol / 48 h / 20 °C

2.1: 95 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH₂Cl₂ / 5 h / 20 °C

3.1: potassium bis(trimethylsilyl)amide / dimethylformamide; toluene / 1 h / -78 °C

3.2: 80 percent / dimethylformamide; toluene / 15 h / -78 - 20 °C

4.1: 62 percent / (dba)3Pd₂*CHCl₃; Et₃N / tetrahydrofuran; CH₂Cl₂ / -78 - 20 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; dipyridinium dichromate; 4 A molecular sieve; hydrogen; potassium hexamethylsilazane; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Suzuki cross-coupling;
DOI:10.1021/jm0501836