(2S,3R,4R,5R) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohexane-1-one

Base Information

Chemical Name:(2S,3R,4R,5R) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohexane-1-one
CAS No.:159701-13-0
Molecular Formula:C₃₃H₄₂O₅Si
Molecular Weight:546.779
Hs Code.:

Synonyms:(2S,3R,4R,5R) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohexane-1-one

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Chemical Property of (2S,3R,4R,5R) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohexane-1-one

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Technology Process of (2S,3R,4R,5R) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohexane-1-one

There total 5 articles about (2S,3R,4R,5R) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohexane-1-one 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: 94.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 87984-31-4
(2S,3R,4S,5R) 5-hydroxy-2,3,4-tris(benzyloxy) cyclohexane-1-one

: 159701-13-0
(2S,3R,4R,5R) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohexane-1-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1016/S0040-4020(01)89584-3

Reference yield: 49.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 606930-14-7
(2S,3R,4S)-2,3,4-tris-benzyloxy-5-hydroxycyclohexan-1-one

: 131289-28-6
(2S,3R,4R,5S) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohexane-1-one

: 159701-13-0
(2S,3R,4R,5R) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohexane-1-one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃;
DOI:10.1021/acschembio.0c00409

Reference yield:

: 100-39-0
benzyl bromide

: 159701-13-0
(2S,3R,4R,5R) 5-<(t-butyldimethylsilyl)oxy>-2,3,4-tris(benzyloxy) cyclohexane-1-one

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) NaH; 2.) n-Bu₄NI / 1.) THF, r.t., 1 h, 60 deg C, 1 h; 2.) THF, r.t., 1 h, 40 deg C, 1 h

2: 18 percent / Hg(OAc)2 / acetone; acetic acid; H₂O / 5 h / Heating

3: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / Ambient temperature

With 2,6-dimethylpyridine; mercury(II) diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; In dichloromethane; water; acetic acid; acetone;
DOI:10.1016/S0040-4020(01)89584-3