Benzoic acid (1R,2R)-1-((4aS,5S,6R)-5-formyl-6-hydroxymethyl-4a,5-dimethyl-2-oxo-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

Base Information

• Chemical Name: Benzoic acid (1R,2R)-1-((4aS,5S,6R)-5-formyl-6-hydroxymethyl-4a,5-dimethyl-2-oxo-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester
• CAS No.: 314280-69-8
• Molecular Formula: C₂₉H₃₈O₆S
• Molecular Weight: 514.683

Synonyms:Benzoic acid (1R,2R)-1-((4aS,5S,6R)-5-formyl-6-hydroxymethyl-4a,5-dimethyl-2-oxo-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

Chemical Property of Benzoic acid (1R,2R)-1-((4aS,5S,6R)-5-formyl-6-hydroxymethyl-4a,5-dimethyl-2-oxo-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (1R,2R)-1-((4aS,5S,6R)-5-formyl-6-hydroxymethyl-4a,5-dimethyl-2-oxo-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

There total 10 articles about Benzoic acid (1R,2R)-1-((4aS,5S,6R)-5-formyl-6-hydroxymethyl-4a,5-dimethyl-2-oxo-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-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: 80.0%

Benzoic acid (1R,2R)-1-((1S,3aR,9aS,9bS)-1-methoxy-9a,9b-dimethyl-7-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 (314281-06-6) → Benzoic acid (1R,2R)-1-((4aS,5S,6R)-5-formyl-6-hydroxymethyl-4a,5-dimethyl-2-oxo-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester (314280-69-8)

Guidance literature:

With perchloric acid; In acetonitrile; at 60 ℃; for 0.25h;

DOI:10.1021/ja034842k

Reference yield: 74.0%

Benzoic acid (1R,2R)-1-((1R,3aR,9aS,9bS)-1-methoxy-9a,9b-dimethyl-7-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 (314281-04-4) → Benzoic acid (1R,2R)-1-((4aS,5S,6R)-5-formyl-6-hydroxymethyl-4a,5-dimethyl-2-oxo-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester (314280-69-8)

Guidance literature:

With perchloric acid; In acetonitrile; at 55 ℃; for 2h;

DOI:10.1021/ja034842k

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (1R,2R)-1-((4aS,5S,6R)-5-formyl-6-hydroxymethyl-4a,5-dimethyl-2-oxo-2,3,4,4a,5,6,7,8-octahydro-naphthalen-1-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester (314280-69-8)

Guidance literature:

Multi-step reaction with 3 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

With dmap; perchloric acid; sodium acetate; acetic acid; In dichloromethane; acetonitrile; benzene;

DOI:10.1021/ja034842k

upstream raw materials:

Benzoic acid (1R,2R)-1-((1R,3aR,9aS,9bS)-1-methoxy-9a,9b-dimethyl-7-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

Benzoic acid (1R,2R)-1-((1S,3aR,9aS,9bS)-1-methoxy-9a,9b-dimethyl-7-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

benzoyl chloride

(R)-2-((R)-2-Methyl-1-methylsulfanylmethoxy-allyl)-oxirane

Downstream raw materials:

Benzoic acid (2R,3R,5S,8S,13R,14S)-3-isopropenyl-8,14-dimethyl-15-oxo-1,2,3,6,7,8,11,12,13,14,15,17-dodecahydro-5H-4,16-dioxa-cyclopenta[a]phenanthren-2-yl ester

C₄₅H₅₂N₂O₇Se

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

Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-7-hydroxy-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

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