(3R,6S,8R,10S,Z)-3-(benzyloxymethyl)-10-(tert-butyldimethylsilyloxy)-11-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-8-methoxy-5,11-dimethyldodec-4-en-6-ol

Base Information

• Chemical Name: (3R,6S,8R,10S,Z)-3-(benzyloxymethyl)-10-(tert-butyldimethylsilyloxy)-11-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-8-methoxy-5,11-dimethyldodec-4-en-6-ol
• CAS No.: 1466415-28-0
• Molecular Formula: C₅₂H₈₂O₆Si₂
• Molecular Weight: 859.39

Synonyms:(3R,6S,8R,10S,Z)-3-(benzyloxymethyl)-10-(tert-butyldimethylsilyloxy)-11-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-8-methoxy-5,11-dimethyldodec-4-en-6-ol

Chemical Property of (3R,6S,8R,10S,Z)-3-(benzyloxymethyl)-10-(tert-butyldimethylsilyloxy)-11-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-8-methoxy-5,11-dimethyldodec-4-en-6-ol

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Technology Process of (3R,6S,8R,10S,Z)-3-(benzyloxymethyl)-10-(tert-butyldimethylsilyloxy)-11-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-8-methoxy-5,11-dimethyldodec-4-en-6-ol

There total 1 articles about (3R,6S,8R,10S,Z)-3-(benzyloxymethyl)-10-(tert-butyldimethylsilyloxy)-11-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-8-methoxy-5,11-dimethyldodec-4-en-6-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: 65.0%

(R,Z)-((2-ethyl-4-iodopent-3-enyloxy)methyl)benzene (1211323-43-1) + (3S,5S)-5-(tert-butyldimethylsilyloxy)-6-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-3-methoxy-6-methylheptanal (1466415-27-9) → (3R,6S,8R,10S,Z)-3-(benzyloxymethyl)-10-(tert-butyldimethylsilyloxy)-11-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-8-methoxy-5,11-dimethyldodec-4-en-6-ol (1466415-28-0) + (R)-(+)-4-(benzyloxymethyl)hexan-2-one

Guidance literature:

(R,Z)-((2-ethyl-4-iodopent-3-enyloxy)methyl)benzene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.666667h;

(3S,5S)-5-(tert-butyldimethylsilyloxy)-6-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-3-methoxy-6-methylheptanal; In diethyl ether; pentane; at 78 ℃; for 14h;

DOI:10.1002/chem.201301796

Reference yield: 87.0%

3,4-dihydro-2H-pyran (110-87-2) + (3R,6S,8R,10S,Z)-3-(benzyloxymethyl)-10-(tert-butyldimethylsilyloxy)-11-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-8-methoxy-5,11-dimethyldodec-4-en-6-ol (1466415-28-0) + (R)-(+)-4-(benzyloxymethyl)hexan-2-one → 2-{(2R,6S)-6-[(3S,5R,7S,10R,Z)-10-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,8-dimethyl-7-(tetrahydro-2H-pyran-2-yloxy)dodec-8-en-2-yl]tetrahydro-2H-pyran-2-yl}ethanol

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1002/chem.201301796

Reference yield: 76.0%

(3R,6S,8R,10S,Z)-3-(benzyloxymethyl)-10-(tert-butyldimethylsilyloxy)-11-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-8-methoxy-5,11-dimethyldodec-4-en-6-ol (1466415-28-0) + (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) → (R)-(3R,6S,8R,10S,Z)-3-(benzyloxymethyl)-10-(tert-butyldimethylsilyloxy)-11-{(2S,6R)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]tetrahydro-2H-pyran-2-yl}-8-meth-oxy-5,11-dimethyldodec-4-en-6-yl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate (1466415-30-4)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1002/chem.201301796

upstream raw materials:

(R,Z)-((2-ethyl-4-iodopent-3-enyloxy)methyl)benzene

(3S,5S)-5-(tert-butyldimethylsilyloxy)-6-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-3-methoxy-6-methylheptanal

Downstream raw materials:

(4S,5R)-3-{(2S,3R)-2-benzyloxy-4-[(2R,6S)-6-((3S,5R,7S,10R,Z)-10-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-5-methoxy-2,8-dimethyldodec-8-en-2-yl)tetrahydro-2H-pyran-2-yl]-3-methoxybutanoyl}-4-methyl-5-phenyloxazolidin-2-one

(2S,3R)-2-benzyloxy-4-{(2R,6S)-6-[(3S,5R,7S,10R,Z)-10-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-5-methoxy-2,8-dimethyldodec-8-en-2-yl] tetrahydro-2H-pyran-2-yl}-3-methoxybutanoic acid

(S)-(3R,6S,8R,10S,Z)-3-(benzyloxymethyl)-10-(tert-butyldimethylsilyloxy)-11-{(2S,6R)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]tetrahydro-2H-pyran-2-yl}-8-methoxy-5,11-dimethyldodec-4-en-6-yl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

(R)-(3R,6S,8R,10S,Z)-3-(benzyloxymethyl)-10-(tert-butyldimethylsilyloxy)-11-{(2S,6R)-6-[2-(tert-butyldiphenylsilyloxy)ethyl]tetrahydro-2H-pyran-2-yl}-8-meth-oxy-5,11-dimethyldodec-4-en-6-yl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

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