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

Base Information

• Chemical Name: Benzoic acid (2R,3S,8S,13R,14S)-3-(1-benzyloxy-1-methyl-ethyl)-8,14-dimethyl-15-oxo-1,2,3,6,8,12,13,14,15,17-decahydro-7H-4,16-dioxa-cyclopenta[a]phenanthren-2-yl ester
• CAS No.: 502614-18-8
• Molecular Formula: C₃₄H₃₈O₆
• Molecular Weight: 542.672

Synonyms:Benzoic acid (2R,3S,8S,13R,14S)-3-(1-benzyloxy-1-methyl-ethyl)-8,14-dimethyl-15-oxo-1,2,3,6,8,12,13,14,15,17-decahydro-7H-4,16-dioxa-cyclopenta[a]phenanthren-2-yl ester

Chemical Property of Benzoic acid (2R,3S,8S,13R,14S)-3-(1-benzyloxy-1-methyl-ethyl)-8,14-dimethyl-15-oxo-1,2,3,6,8,12,13,14,15,17-decahydro-7H-4,16-dioxa-cyclopenta[a]phenanthren-2-yl ester

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Technology Process of Benzoic acid (2R,3S,8S,13R,14S)-3-(1-benzyloxy-1-methyl-ethyl)-8,14-dimethyl-15-oxo-1,2,3,6,8,12,13,14,15,17-decahydro-7H-4,16-dioxa-cyclopenta[a]phenanthren-2-yl ester

There total 26 articles about Benzoic acid (2R,3S,8S,13R,14S)-3-(1-benzyloxy-1-methyl-ethyl)-8,14-dimethyl-15-oxo-1,2,3,6,8,12,13,14,15,17-decahydro-7H-4,16-dioxa-cyclopenta[a]phenanthren-2-yl 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: 82.0%

Benzoic acid (2R,3S,8S,13R,14S)-3-(1-benzyloxy-1-methyl-ethyl)-15-hydroxy-8,14-dimethyl-1,2,3,6,8,12,13,14,15,17-decahydro-7H-4,16-dioxa-cyclopenta[a]phenanthren-2-yl ester → Benzoic acid (2R,3S,8S,13R,14S)-3-(1-benzyloxy-1-methyl-ethyl)-8,14-dimethyl-15-oxo-1,2,3,6,8,12,13,14,15,17-decahydro-7H-4,16-dioxa-cyclopenta[a]phenanthren-2-yl ester (502614-18-8)

Guidance literature:

With tris(triphenylphosphine)ruthenium(II) chloride; triethylamine; 1-Phenylbut-1-en-3-one; In toluene; at 110 ℃;

DOI:10.1021/ol027575g

Reference yield: 30.0%

(+)-(1R,2S)-3-(benzyloxy)-1-{[(9aS,9bS)-1,3,3a,4,5,7,8,9,9a,9b-decahydro-9a,9b-dimethyl-1,7-dioxonaphtho[1,2-c]furan-6-yl]methyl}-3-methyl-2-[(methylsulfanyl)methoxy]butyl benzenecarboxylate (502613-93-6) → (-)-(2S,3R,9aS,9bS,11aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-9a,9b-dimethyl-9-oxo-2H-[2]benzofuro[5,4-f][1]benzopyran-3-yl benzenecarboxylate (502613-94-7) + Benzoic acid (2R,3S,8S,13R,14S)-3-(1-benzyloxy-1-methyl-ethyl)-8,14-dimethyl-15-oxo-1,2,3,6,8,12,13,14,15,17-decahydro-7H-4,16-dioxa-cyclopenta[a]phenanthren-2-yl ester (502614-18-8)

Guidance literature:

With triethylsilane; trifluorormethanesulfonic acid; In dichloromethane; acetonitrile; at -40 - -5 ℃;

DOI:10.1002/hlca.200390328

Reference yield:

Benzoic acid (1R,2S)-3-benzyloxy-2-hydroxy-1-((3aR,9aS,9bS)-1-hydroxy-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-butyl ester → Benzoic acid (2R,3S,8S,13R,14S)-3-(1-benzyloxy-1-methyl-ethyl)-8,14-dimethyl-15-oxo-1,2,3,6,8,12,13,14,15,17-decahydro-7H-4,16-dioxa-cyclopenta[a]phenanthren-2-yl ester (502614-18-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / HCl / tetrahydrofuran; H₂O

2: 82 percent / (PPh₃)3RuCl₂; triethylamine; CH₃COCHCHPh / toluene / 110 °C

With hydrogenchloride; tris(triphenylphosphine)ruthenium(II) chloride; triethylamine; 1-Phenylbut-1-en-3-one; In tetrahydrofuran; water; toluene;

DOI:10.1021/ol027575g

upstream raw materials:

(+)-(1R,2S)-3-(benzyloxy)-1-{[(9aS,9bS)-1,3,3a,4,5,7,8,9,9a,9b-decahydro-9a,9b-dimethyl-1,7-dioxonaphtho[1,2-c]furan-6-yl]methyl}-3-methyl-2-[(methylsulfanyl)methoxy]butyl benzenecarboxylate

benzoyl chloride

(2R,3R)-1,2-O-isopropylidene-4-methyl-4-pentene-1,2,3-triol

C₂₂H₄₀O₃Si

Downstream raw materials:

(-)-(2S,3R,9aS,9bS,11aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,6a,7,9,9a,9b,10,11,11a-dodecahydro-9a,9b-dimethyl-9-oxo-2H-[2]benzofuro[5,4-f][1]benzopyran-3-yl benzenecarboxylate

(+)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-3-hydroxy-10a,10b-dimethyl-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

(-)-(2S,3R,4aR,5aS,10aS,10bRS,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-10a,10b-dimethyl-10-oxo-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-3-yl benzenecarboxylate

(-)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-10a,10b-dimethyl-3-[(triethylsilyl)oxy]-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

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