(2S,3R,4aS,6R,7S,8aR)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-isopropenyl-7-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran

Base Information

Chemical Name:(2S,3R,4aS,6R,7S,8aR)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-isopropenyl-7-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran
CAS No.:889109-08-4
Molecular Formula:C₃₆H₆₄O₆Si₂
Molecular Weight:649.072
Hs Code.:

(2S,3R,4aS,6R,7S,8aR)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-isopropenyl-7-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran

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Chemical Property of (2S,3R,4aS,6R,7S,8aR)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-isopropenyl-7-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran

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Technology Process of (2S,3R,4aS,6R,7S,8aR)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-isopropenyl-7-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran

There total 7 articles about (2S,3R,4aS,6R,7S,8aR)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-isopropenyl-7-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran 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:

: 858346-53-9
(2R,4aR,6R,7S,8aR,9aS,10aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

: 889109-08-4
(2S,3R,4aS,6R,7S,8aR)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-isopropenyl-7-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 7 steps

1.1: H₂ / Pd(OH)2/C / ethyl acetate / 4 h

2.1: 77 percent / KH / tetrahydrofuran / 2 h / 35 °C

3.1: 100 percent / HMDS; TMSI / CH₂Cl₂ / 1 h / 0 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: tetrahydrofuran / 0.5 h / 0 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: NaHMDS / tetrahydrofuran / 0 °C

7.2: 298 mg / tetrahydrofuran / 1 h / 20 °C

With oxalyl dichloride; trimethylsilyl iodide; hydrogen; sodium hexamethyldisilazane; potassium hydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; 4.1: Swern oxidation / 5.1: Grignard reaction / 6.1: Swern oxidation / 7.2: Wittig reaction;
DOI:10.1021/jo0603025

Reference yield:

: 1-[(2S,3S,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-(4-methoxy-benzyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-ethanone

: 1779-49-3
Methyltriphenylphosphonium bromide

: 889109-08-4
(2S,3R,4aS,6R,7S,8aR)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-isopropenyl-7-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃;

1-[(2S,3S,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-3-(4-methoxy-benzyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-ethanone; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/jo0603025

Reference yield:

: (2R,3S,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-hydroxymethyl-8a-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

: 889109-08-4
(2S,3R,4aS,6R,7S,8aR)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-6-isopropenyl-7-(4-methoxy-benzyloxy)-4a-methyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 6 steps

1.1: 77 percent / KH / tetrahydrofuran / 2 h / 35 °C

2.1: 100 percent / HMDS; TMSI / CH₂Cl₂ / 1 h / 0 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: tetrahydrofuran / 0.5 h / 0 °C

5.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: NaHMDS / tetrahydrofuran / 0 °C

6.2: 298 mg / tetrahydrofuran / 1 h / 20 °C

With oxalyl dichloride; trimethylsilyl iodide; sodium hexamethyldisilazane; potassium hydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation / 4.1: Grignard reaction / 5.1: Swern oxidation / 6.2: Wittig reaction;
DOI:10.1021/jo0603025