1-[(2R,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]-ethanol

Base Information

• Chemical Name: 1-[(2R,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]-ethanol
• CAS No.: 889109-07-3
• Molecular Formula: C₃₅H₆₄O₇Si₂
• Molecular Weight: 653.06

Synonyms:1-[(2R,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]-ethanol

Chemical Property of 1-[(2R,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]-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 1-[(2R,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]-ethanol

There total 5 articles about 1-[(2R,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]-ethanol 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:

(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 (858346-53-9) → 1-[(2R,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]-ethanol (889109-07-3)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 100 percent / HMDS; TMSI / CH₂Cl₂ / 1 h / 0 °C

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

5: tetrahydrofuran / 0.5 h / 0 °C

With oxalyl dichloride; trimethylsilyl iodide; hydrogen; potassium hydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; palladium dihydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; 4: Swern oxidation / 5: Grignard reaction;

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 → 1-[(2R,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]-ethanol (889109-07-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / KH / tetrahydrofuran / 2 h / 35 °C

2: 100 percent / HMDS; TMSI / CH₂Cl₂ / 1 h / 0 °C

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

4: tetrahydrofuran / 0.5 h / 0 °C

With oxalyl dichloride; trimethylsilyl iodide; potassium hydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; 3: Swern oxidation / 4: Grignard reaction;

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]-3-(4-methoxy-benzyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol (889109-06-2) → 1-[(2R,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]-ethanol (889109-07-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: tetrahydrofuran / 0.5 h / 0 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Swern oxidation / 2: Grignard reaction;

DOI:10.1021/jo0603025

upstream raw materials:

methyl magnesium iodide

(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

[(2R,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]-methanol

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

Downstream raw materials:

tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-4a,5-dimethyl-2-((R)-2-methyl-3-phenylsulfanyl-propyl)-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

tert-Butyl-[(2S,3R,4aS,8aS,9aR,10aR)-2-((R)-3-chloro-2-methyl-3-phenylsulfanyl-propyl)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-3-yloxy]-dimethyl-silane

(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

C₄₇H₆₂O₉

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