Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-acetoxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-2-hydroxy-3-methyl-but-3-enyl ester

Base Information

Chemical Name:Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-acetoxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-2-hydroxy-3-methyl-but-3-enyl ester
CAS No.:573699-15-7
Molecular Formula:C₂₉H₃₆O₇
Molecular Weight:496.601
Hs Code.:

Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-acetoxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-2-hydroxy-3-methyl-but-3-enyl ester

Synonyms:Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-acetoxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-2-hydroxy-3-methyl-but-3-enyl ester

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Chemical Property of Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-acetoxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-2-hydroxy-3-methyl-but-3-enyl ester

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Technology Process of Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-acetoxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-2-hydroxy-3-methyl-but-3-enyl ester

There total 14 articles about Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-acetoxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-2-hydroxy-3-methyl-but-3-enyl 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: 99.0%

: 573699-32-8
Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-acetoxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

: 573699-15-7
Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-acetoxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-2-hydroxy-3-methyl-but-3-enyl ester

Guidance literature:: With calcium carbonate; methyl iodide; In tetrahydrofuran; acetonitrile; at 55 ℃;
DOI:10.1021/ja034842k

Reference yield:

: 98-88-4
benzoyl chloride

: 573699-15-7
Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-acetoxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-2-hydroxy-3-methyl-but-3-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 60 percent / DMAP / CH₂Cl₂ / 18 h / 20 °C

2: 56 percent / NaOAc; AcOH / benzene / 14 h / 65 °C

3: 74 percent / aq. perchloric acid / acetonitrile / 2 h / 55 °C

4: 78 percent / pyridinium dichromate / CH₂Cl₂ / 5 h / 20 °C

5: 85 percent / NaBH₄; CeCl₃ / methanol / 0 °C

6: 94 percent / DMAP; Et₃N / CH₂Cl₂

7: 99 percent / MeI; aq. CaCO₃ / acetonitrile; tetrahydrofuran / 55 °C

With dmap; sodium tetrahydroborate; dipyridinium dichromate; perchloric acid; cerium(III) chloride; sodium acetate; acetic acid; triethylamine; calcium carbonate; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; benzene;
DOI:10.1021/ja034842k

Reference yield:

: 251305-18-7
(R)-2-((R)-2-Methyl-1-methylsulfanylmethoxy-allyl)-oxirane

: 573699-15-7
Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-acetoxy-9a,9b-dimethyl-1-oxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-2-hydroxy-3-methyl-but-3-enyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: LDA; (+)-4,4a,5,6,7,8-hexahydro-4a-Me-2(3H)-Nph dimethylhydrazone / tetrahydrofuran / 6 h / -78 - 65 °C

1.2: tetrahydrofuran / 3.5 h

2.1: 76 percent / DMAP / CH₂Cl₂ / 23 h / 20 °C

3.1: 53 percent / NaOAc; AcOH / benzene / 16 h / 65 °C

4.1: 80 percent / aq. perchloric acid / acetonitrile / 0.25 h / 60 °C

5.1: 78 percent / pyridinium dichromate / CH₂Cl₂ / 5 h / 20 °C

6.1: 85 percent / NaBH₄; CeCl₃ / methanol / 0 °C

7.1: 94 percent / DMAP; Et₃N / CH₂Cl₂

8.1: 99 percent / MeI; aq. CaCO₃ / acetonitrile; tetrahydrofuran / 55 °C

With dmap; sodium tetrahydroborate; dipyridinium dichromate; perchloric acid; cerium(III) chloride; (+)-4,4a,5,6,7,8-hexahydro-4a-Me-2(3H)-Nph dimethylhydrazone; sodium acetate; acetic acid; triethylamine; calcium carbonate; lithium diisopropyl amide; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; benzene; 1.1: Stork metalloenamine alkylation;
DOI:10.1021/ja034842k