(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

Base Information

• Chemical Name: (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
• CAS No.: 145745-98-8
• Molecular Formula: C₂₇H₃₄O₈
• Molecular Weight: 486.562

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 51 articles about (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 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%

(2aR*,3S*,5R*,5aS*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-oxo-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate (138175-79-8) → (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)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 0.25h;

DOI:10.1039/P19920002735

Reference yield: 44.0%

(2aR*,3S*,5R*,5aS*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-oxo-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate (138175-79-8) → (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*,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)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; for 0.166667h;

DOI:10.1039/P19920002735

Reference yield: 44.0%

(2aR*,3S*,5R*,5aS*,8aS*,8bS*)-methyl 3,5-<(S*)-benzylidenedioxy>-8-oxo-5a-(2'-pivaloyloxyethyl)-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate (138175-79-8) → (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*,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)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; for 0.166667h;

DOI:10.1039/P19920002735

upstream raw materials:

pivaloyl chloride

(2aR,3S,5R,5aS,8R,8aS,8bS)-methyl 3,5-<(R)-benzylidenedioxy>-5a-(2'-pivaloyloxyethyl)-8-<(1''S,4''R)-4'',7'',7''-trimethyl-3''-oxo-2''-oxabicyclo<2.2.1>heptan-1''-ylcarbonyloxy>-4,5,5a,8,8a,8b-hexahydro-2H,3H-naphtho<1,8-bc>furan-2a-carboxylate

(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

(2aR*,3R*,4aR*,7aS*,8S*,10aR*,10bR*)-methyl 3-dimethyl(phenyl)silyl-8-hydroxy-4a-methoxyperhydronaphtho<1,8-bc:5,4a-b'>difuran-10-spiro-2'-(1',3'-dithiane)-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>-8-tert-butyldimethylsiloxy-5a-(2'-hydroxyethyl)-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

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