(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

Base Information

Chemical Name:(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
CAS No.:438547-32-1
Molecular Formula:C₄₂H₄₂N₂O₁₀S₂
Molecular Weight:798.935
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 11 articles about (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 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:

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

: 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

Guidance literature:: Multi-step reaction with 10 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

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

: 438547-32-1
(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

Guidance literature:: Multi-step reaction with 9 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

With pyridine; 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

Reference yield:

: 108-98-5
thiophenol

: 688045-93-4
9-benzyloxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-10-methylene-5-(2-nitro-benzenesulfonyl)-3a,5,10,11a-tetrahydro-4H-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-11-one

: 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

Guidance literature:: thiophenol; 9-benzyloxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-10-methylene-5-(2-nitro-benzenesulfonyl)-3a,5,10,11a-tetrahydro-4H-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-11-one; With triethylamine; In tetrahydrofuran; methanol; at 20 ℃; for 3h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 0.25h;
DOI:10.1021/jo049862z