Acetic acid (3aR,10R,11R,11aR)-9-benzyloxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-10-phenylsulfanylmethyl-3a,4,5,10,11,11a-hexahydro-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-11-yl ester

Base Information

Chemical Name:Acetic acid (3aR,10R,11R,11aR)-9-benzyloxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-10-phenylsulfanylmethyl-3a,4,5,10,11,11a-hexahydro-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-11-yl ester
CAS No.:438547-33-2
Molecular Formula:C₄₄H₄₄N₂O₁₁S₂
Molecular Weight:840.972
Hs Code.:

Acetic acid (3aR,10R,11R,11aR)-9-benzyloxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-10-phenylsulfanylmethyl-3a,4,5,10,11,11a-hexahydro-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-11-yl ester

Synonyms:Acetic acid (3aR,10R,11R,11aR)-9-benzyloxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-10-phenylsulfanylmethyl-3a,4,5,10,11,11a-hexahydro-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-11-yl ester

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Chemical Property of Acetic acid (3aR,10R,11R,11aR)-9-benzyloxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-10-phenylsulfanylmethyl-3a,4,5,10,11,11a-hexahydro-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-11-yl ester

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Technology Process of Acetic acid (3aR,10R,11R,11aR)-9-benzyloxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-10-phenylsulfanylmethyl-3a,4,5,10,11,11a-hexahydro-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-11-yl ester

There total 12 articles about Acetic acid (3aR,10R,11R,11aR)-9-benzyloxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-10-phenylsulfanylmethyl-3a,4,5,10,11,11a-hexahydro-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-11-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: 80.0%

: 108-24-7
acetic anhydride

: 438547-32-1
(3aR,10R,11R,11aR)-9-Benzyloxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-10-phenylsulfanylmethyl-3a,4,5,10,11,11a-hexahydro-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-11-ol

: 438547-33-2
Acetic acid (3aR,10R,11R,11aR)-9-benzyloxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-10-phenylsulfanylmethyl-3a,4,5,10,11,11a-hexahydro-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-11-yl ester

Guidance literature:: With pyridine; dmap; at 20 ℃; for 2.5h;
DOI:10.1021/jo049862z

Reference yield:

: methyl 3-benzyloxy-4-{2-[(4R,5R)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethyl}-5-nitrobenzoate

: 438547-33-2
Acetic acid (3aR,10R,11R,11aR)-9-benzyloxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-10-phenylsulfanylmethyl-3a,4,5,10,11,11a-hexahydro-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-11-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 9.8 g / pyridine; DMAP / 3 h / 20 °C

2.1: 65 percent / H₂ / Pt/C / methanol / 52 h / 20 °C / 760 Torr

3.1: 73 percent / pyridine / 1 h / 20 °C

4.1: TBAF / tetrahydrofuran / 41 h / 20 °C

5.1: 1.15 g / Ph₃P; DEAD / benzene; toluene / 1 h / 20 °C

6.1: DIBAL / CH₂Cl₂; toluene / 1.25 h / -78 °C

7.1: 21.2 g / Ph₃P; DEAD / benzene; toluene / 0.33 h / 20 °C

8.1: 72 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

9.1: Me₂NH*HCl; Et₃N / H₂O; propan-2-ol / 4.5 h / 90 °C

10.1: Et₃N / tetrahydrofuran; methanol / 3 h / 20 °C

10.2: 15.0 g / NaBH₄ / tetrahydrofuran; methanol / 0.25 h / 0 °C

11.1: 80 percent / pyridine; DMAP / 2.5 h / 20 °C

With pyridine; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; N,N-dimethylammonium chloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; platinum on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; toluene; benzene; 8.1: Swern oxidation / 10.1: Michael addition;
DOI:10.1021/jo049862z

Reference yield:

: 438547-26-3
methyl 4-{(2R)-2-acetoxy-2-[(4S,5R)-5-(tert-butyldimethylsilyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl}-3-benzyloxy-5-nitrobenzoate

: 438547-33-2
Acetic acid (3aR,10R,11R,11aR)-9-benzyloxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-10-phenylsulfanylmethyl-3a,4,5,10,11,11a-hexahydro-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-11-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 65 percent / H₂ / Pt/C / methanol / 52 h / 20 °C / 760 Torr

2.1: 73 percent / pyridine / 1 h / 20 °C

3.1: TBAF / tetrahydrofuran / 41 h / 20 °C

4.1: 1.15 g / Ph₃P; DEAD / benzene; toluene / 1 h / 20 °C

5.1: DIBAL / CH₂Cl₂; toluene / 1.25 h / -78 °C

6.1: 21.2 g / Ph₃P; DEAD / benzene; toluene / 0.33 h / 20 °C

7.1: 72 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: Me₂NH*HCl; Et₃N / H₂O; propan-2-ol / 4.5 h / 90 °C

9.1: Et₃N / tetrahydrofuran; methanol / 3 h / 20 °C

9.2: 15.0 g / NaBH₄ / tetrahydrofuran; methanol / 0.25 h / 0 °C

10.1: 80 percent / pyridine; DMAP / 2.5 h / 20 °C

With pyridine; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; N,N-dimethylammonium chloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; platinum on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; toluene; benzene; 7.1: Swern oxidation / 9.1: Michael addition;
DOI:10.1021/jo049862z