(1R,3S,4R,4aR,5R,6R,8aR)-3,4-Bis-benzoyloxy-5,8a-dimethyl-5-[2-(tetrahydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1,6-dicarboxylic acid dimethyl ester

Base Information

Chemical Name:(1R,3S,4R,4aR,5R,6R,8aR)-3,4-Bis-benzoyloxy-5,8a-dimethyl-5-[2-(tetrahydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1,6-dicarboxylic acid dimethyl ester
CAS No.:131574-97-5
Molecular Formula:C₃₆H₄₄O₉
Molecular Weight:620.74
Hs Code.:

(1R,3S,4R,4aR,5R,6R,8aR)-3,4-Bis-benzoyloxy-5,8a-dimethyl-5-[2-(tetrahydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1,6-dicarboxylic acid dimethyl ester

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Chemical Property of (1R,3S,4R,4aR,5R,6R,8aR)-3,4-Bis-benzoyloxy-5,8a-dimethyl-5-[2-(tetrahydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1,6-dicarboxylic acid dimethyl ester

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Technology Process of (1R,3S,4R,4aR,5R,6R,8aR)-3,4-Bis-benzoyloxy-5,8a-dimethyl-5-[2-(tetrahydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1,6-dicarboxylic acid dimethyl ester

There total 7 articles about (1R,3S,4R,4aR,5R,6R,8aR)-3,4-Bis-benzoyloxy-5,8a-dimethyl-5-[2-(tetrahydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1,6-dicarboxylic acid dimethyl ester 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: 95.0%

: (1R,3S,4R,4aR,5R,6R,8aR)-4-Benzoyloxy-3-hydroxy-5,8a-dimethyl-5-[2-(tetrahydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1,6-dicarboxylic acid dimethyl ester

: 98-88-4
benzoyl chloride

: 131574-97-5
(1R,3S,4R,4aR,5R,6R,8aR)-3,4-Bis-benzoyloxy-5,8a-dimethyl-5-[2-(tetrahydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1,6-dicarboxylic acid dimethyl ester

Guidance literature:: With pyridine; for 2h; Ambient temperature;
DOI:10.1246/cl.1990.2015

Reference yield: 50.0%

: 36967-85-8
benzoyl triflate

: 131574-96-4
(1R,3S,4R,4aR,5R,6R,8aR)-3,4-Dihydroxy-5,8a-dimethyl-5-[2-(tetrahydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1,6-dicarboxylic acid dimethyl ester

: 131574-97-5
(1R,3S,4R,4aR,5R,6R,8aR)-3,4-Bis-benzoyloxy-5,8a-dimethyl-5-[2-(tetrahydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1,6-dicarboxylic acid dimethyl ester

Guidance literature:: With pyridine; In dichloromethane; for 1h; 1) -78 deg C to RT, 2) 1h, RT;
DOI:10.1246/cl.1990.2015

Reference yield:

: 83729-01-5
salvinorin A

: 131574-97-5
(1R,3S,4R,4aR,5R,6R,8aR)-3,4-Bis-benzoyloxy-5,8a-dimethyl-5-[2-(tetrahydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1,6-dicarboxylic acid dimethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: H₂ / 5percent Pd/C / methanol / 14 h

2: methanol / 2 h / 0 °C

3: KCN / methanol / 0.25 h / Heating

4: 81 percent / NaBH₄ / ethanol / 12 h / 0 deg C to RT

5: 50 percent / pyridine / CH₂Cl₂ / 1 h / 1) -78 deg C to RT, 2) 1h, RT

With pyridine; potassium cyanide; sodium tetrahydroborate; hydrogen; palladium on activated charcoal; In methanol; ethanol; dichloromethane;
DOI:10.1246/cl.1990.2015