(3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-one

Base Information

Chemical Name:(3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-one
CAS No.:774599-32-5
Molecular Formula:C₄₀H₅₀O₆Si
Molecular Weight:654.919
Hs Code.:

Synonyms:(3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-one

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Chemical Property of (3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-one

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Technology Process of (3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-one

There total 1 articles about (3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-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: 84.0%

: 158535-90-1
1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-L-galactitol

: 774599-32-5
(3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-one

Guidance literature:: 1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-L-galactitol; With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; at -78 ℃; for 2.5h;

With triethylamine; at -78 ℃; for 0.25h;
DOI:10.1021/ol0490779

Reference yield:

: 774599-32-5
(3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-one

: 1034-49-7
(bromomethyl)triphenyl phosphonium bromide

: 774599-17-6
tert-Butyl-dimethyl-((Z)-(2S,3S,4S)-2,3,4-tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enyloxy)-silane

: tert-Butyl-dimethyl-((E)-(2S,3S,4S)-2,3,4-tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enyloxy)-silane

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; tert-butyl alcohol; at -78 ℃; for 2h;
DOI:10.1021/ol0490779

Reference yield:

: 774599-32-5
(3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-one

: 774599-20-1
(4S,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / -78 °C

2.1: 88 percent / TBAF / tetrahydrofuran / 1 h

3.1: oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 1 h / -78 °C

3.2: 98 percent / Et₃N / 0.42 h / -78 °C

4.1: CrCl₂; NiCl₂ / dimethylformamide / 18 h / 40 °C

4.2: 86 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 20 °C

With chromium dichloride; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; nickel dichloride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Swern oxidation / 4.1: intramolecular Nozaki-Hiyama-Kishi cyclization;
DOI:10.1021/ol0490779