(3S,4S,5R,6R)-2-Allyl-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-ol

Base Information

Chemical Name:(3S,4S,5R,6R)-2-Allyl-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-ol
CAS No.:617673-24-2
Molecular Formula:C₃₄H₄₄O₄Si
Molecular Weight:544.806
Hs Code.:

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

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

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

There total 11 articles about (3S,4S,5R,6R)-2-Allyl-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-ol 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: 87.0%

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

: 1730-25-2
allylmagnesium bromide

: 617673-24-2
(3S,4S,5R,6R)-2-Allyl-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-ol

Guidance literature:: In diethyl ether; at -78 ℃; for 3h;
DOI:10.1016/S0040-4020(03)00873-1

Reference yield:

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

: 617673-24-2
(3S,4S,5R,6R)-2-Allyl-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 7 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

7.1: 87 percent / diethyl ether / 3 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

: 617673-24-2
(3S,4S,5R,6R)-2-Allyl-5-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dimethyl-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 8 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

8.1: 87 percent / diethyl ether / 3 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