(3S,4S,5R,6R)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-one

Base Information

Chemical Name:(3S,4S,5R,6R)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-one
CAS No.:617673-23-1
Molecular Formula:C₃₁H₃₈O₄Si
Molecular Weight:502.726
Hs Code.:

Synonyms:(3S,4S,5R,6R)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-one

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Chemical Property of (3S,4S,5R,6R)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-one

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Technology Process of (3S,4S,5R,6R)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-one

There total 10 articles about (3S,4S,5R,6R)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-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:

: 917-54-4
methyllithium

: 186598-60-7
4-O-benzyl-6-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-threo-hex-2-eno-1,5-aldonolactone

: 74-88-4
methyl iodide

: 617673-23-1
(3S,4S,5R,6R)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-one

: (3R,4S,5R,6R)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-one

Guidance literature:: methyllithium; 4-O-benzyl-6-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-threo-hex-2-eno-1,5-aldonolactone; With copper(l) iodide; chloro-trimethyl-silane; In diethyl ether; at -20 ℃;

methyl iodide; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1016/S0040-4020(03)00873-1

Reference yield:

: 124648-31-3
6-((tert-butyldimethylsilyl)oxy)-3-O-benzoyl-D-galactal

: 617673-23-1
(3S,4S,5R,6R)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 92 percent / NaH / dimethylformamide / 6 h / 0 °C

2.1: 95 percent / TBAG / tetrahydrofuran / 3 h / 20 °C

3.1: 100 percent / imidazole / dimethylformamide / 2 h / 20 °C

4.1: 51 percent / PCC / 1,2-dichloro-ethane / 6 h / 80 °C

5.1: 98 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

6.1: CuI; TMSCl / diethyl ether / -20 °C

6.2: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

With 1H-imidazole; copper(l) iodide; chloro-trimethyl-silane; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(03)00873-1

Reference yield:

: 124751-19-5
(2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

: 617673-23-1
(3S,4S,5R,6R)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 93 percent / pyridine / -35 - 0 °C

2.1: 92 percent / NaH / dimethylformamide / 6 h / 0 °C

3.1: 95 percent / TBAG / tetrahydrofuran / 3 h / 20 °C

4.1: 100 percent / imidazole / dimethylformamide / 2 h / 20 °C

5.1: 51 percent / PCC / 1,2-dichloro-ethane / 6 h / 80 °C

6.1: 98 percent / DBU / CH₂Cl₂ / 2 h / 20 °C

7.1: CuI; TMSCl / diethyl ether / -20 °C

7.2: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

With pyridine; 1H-imidazole; copper(l) iodide; chloro-trimethyl-silane; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(03)00873-1