(2aR*,3S*,5R*,5aS*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-tert-butyldimethylsiloxyl-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

Base Information

• Chemical Name: (2aR*,3S*,5R*,5aS*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-tert-butyldimethylsiloxyl-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate
• CAS No.: 145745-99-9
• Molecular Formula: C₃₃H₄₈O₈Si
• Molecular Weight: 600.825

Synonyms:

Chemical Property of (2aR*,3S*,5R*,5aS*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-tert-butyldimethylsiloxyl-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (2aR*,3S*,5R*,5aS*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-tert-butyldimethylsiloxyl-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

There total 43 articles about (2aR*,3S*,5R*,5aS*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-tert-butyldimethylsiloxyl-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate 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: 97.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2aR*,3S*,5R*,5aS*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-hydroxy-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate (145745-98-8,145840-55-7,145840-73-9,145840-74-0) → (2aR*,3S*,5R*,5aS*,8S*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-tert-butyldimethylsiloxyl-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate (145745-99-9,145840-62-6,145840-75-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 35 ℃; for 2h;

DOI:10.1039/P19920002735

Reference yield: 96.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2aR,3S,5R,5aS,8R,8aS,8bS)-methyl 3,5-<(S)-benzylidenedioxy>-8-hydroxy-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate (145745-98-8,145840-55-7,145840-73-9,145840-74-0) → (2aR,3S,5R,5aS,8R,8aS,8bS)-methyl 3,5-<(S)-benzylidenedioxy>-8-tert-butyldimethylsiloxy-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate (145745-99-9,145840-62-6,145840-75-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.416667h;

DOI:10.1039/P19920002735

Reference yield: 96.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2aS,3R,5S,5aR,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-8-hydroxy-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate (145745-98-8,145840-55-7,145840-73-9,145840-74-0) → (2aS,3R,5S,5aR,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-8-tert-butyldimethylsiloxy-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate (145745-99-9,145840-62-6,145840-75-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.416667h;

DOI:10.1039/P19920002735

upstream raw materials:

t-butyldimethylsiyl triflate

(2aR,3S,5R,5aS,8R,8aS,8bS)-methyl 3,5-<(S)-benzylidenedioxy>-8-hydroxy-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

pivaloyl chloride

(2aR*,3S*,5R*,5aS*,8aS*,8bS*)-methyl 3,5-dihydroxy-8-oxo-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

Downstream raw materials:

(2aR,4aR,5RS,8aR,9S,11R,11aS,11bS)-methyl 9,11-<(R)-benzylidenedioxy>-5-cyano3,6-dioxoperhydrofuro<2',3',4';4,5>naphtho<8a,1-c>pyran-11a-carboxylate

(2aS,3R,5S,5aS,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-8-tert-butyldimethylsiloxy-5a-formyl-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

(2aS,3R,5S,5aR,8S,8aR,8bR)-methyl 3,5-<(R)-benzylidenedioxy>-5a-cyanoacetoxymethyl-8-hydroxy-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

(2aR,4aS,5SR,7aS,8S,10R,10aS,10bR)-dimethyl 8,9-<(R)benzylidenedioxy>-5-hydroxy-3-oxoperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate

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