acetic acid 9-benzyloxy-10-(tert-butyl-dimethyl-silanyloxymethyl)-11-hydroxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-3a,10,11,11a-tetrahydro-4H-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-5-yl ester

Base Information

Chemical Name:acetic acid 9-benzyloxy-10-(tert-butyl-dimethyl-silanyloxymethyl)-11-hydroxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-3a,10,11,11a-tetrahydro-4H-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-5-yl ester
CAS No.:688045-96-7
Molecular Formula:C₃₈H₅₁NO₉Si
Molecular Weight:693.91
Hs Code.:

acetic acid 9-benzyloxy-10-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-11-hydroxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-3a,10,11,11a-tetrahydro-4<i>H</i>-1,3-dioxa-5-aza-benzo[<i>a</i>]cyclopenta[<i>e</i>]cycloocten-5-yl ester

Synonyms:acetic acid 9-benzyloxy-10-(tert-butyl-dimethyl-silanyloxymethyl)-11-hydroxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-3a,10,11,11a-tetrahydro-4H-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-5-yl ester

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Chemical Property of acetic acid 9-benzyloxy-10-(tert-butyl-dimethyl-silanyloxymethyl)-11-hydroxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-3a,10,11,11a-tetrahydro-4H-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-5-yl ester

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Technology Process of acetic acid 9-benzyloxy-10-(tert-butyl-dimethyl-silanyloxymethyl)-11-hydroxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-3a,10,11,11a-tetrahydro-4H-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-5-yl ester

There total 19 articles about acetic acid 9-benzyloxy-10-(tert-butyl-dimethyl-silanyloxymethyl)-11-hydroxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-3a,10,11,11a-tetrahydro-4H-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-5-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:

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

: 688045-96-7
acetic acid 9-benzyloxy-10-(tert-butyl-dimethyl-silanyloxymethyl)-11-hydroxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-3a,10,11,11a-tetrahydro-4H-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-5-yl ester

Guidance literature:: Multi-step reaction with 18 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

12.1: m-CPBA / CH₂Cl₂ / 1 h / -13 °C

13.1: Et₃N; TFAA / toluene / 0.5 h / 0 °C

13.2: 3.90 g / NaBH₄ / toluene; methanol / 1 h / -78 - 20 °C

14.1: DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

15.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

16.1: 4.90 g / Cs₂CO₃; PhSH / acetonitrile / 1 h / 20 °C

17.1: m-CPBA / CH₂Cl₂ / 0.5 h / 20 °C

18.1: 12 h / 20 °C

With pyridine; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; N,N-dimethylammonium chloride; diisobutylaluminium hydride; caesium carbonate; dimethyl sulfoxide; thiophenol; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic anhydride; diethylazodicarboxylate; platinum on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile; 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

: 688045-96-7
acetic acid 9-benzyloxy-10-(tert-butyl-dimethyl-silanyloxymethyl)-11-hydroxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-3a,10,11,11a-tetrahydro-4H-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-5-yl ester

Guidance literature:: Multi-step reaction with 17 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

11.1: m-CPBA / CH₂Cl₂ / 1 h / -13 °C

12.1: Et₃N; TFAA / toluene / 0.5 h / 0 °C

12.2: 3.90 g / NaBH₄ / toluene; methanol / 1 h / -78 - 20 °C

13.1: DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

14.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

15.1: 4.90 g / Cs₂CO₃; PhSH / acetonitrile / 1 h / 20 °C

16.1: m-CPBA / CH₂Cl₂ / 0.5 h / 20 °C

17.1: 12 h / 20 °C

With pyridine; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; N,N-dimethylammonium chloride; diisobutylaluminium hydride; caesium carbonate; dimethyl sulfoxide; thiophenol; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic anhydride; diethylazodicarboxylate; platinum on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile; benzene; 7.1: Swern oxidation / 9.1: Michael addition;
DOI:10.1021/jo049862z

Reference yield:

: 150-76-5
4-methoxy-phenol

: 688045-96-7
acetic acid 9-benzyloxy-10-(tert-butyl-dimethyl-silanyloxymethyl)-11-hydroxy-7-(4-methoxy-phenoxymethyl)-2,2-dimethyl-3a,10,11,11a-tetrahydro-4H-1,3-dioxa-5-aza-benzo[a]cyclopenta[e]cycloocten-5-yl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: 21.2 g / Ph₃P; DEAD / benzene; toluene / 0.33 h / 20 °C

2.1: 72 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

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

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

4.2: 15.0 g / NaBH₄ / tetrahydrofuran; methanol / 0.25 h / 0 °C

5.1: 80 percent / pyridine; DMAP / 2.5 h / 20 °C

6.1: m-CPBA / CH₂Cl₂ / 1 h / -13 °C

7.1: Et₃N; TFAA / toluene / 0.5 h / 0 °C

7.2: 3.90 g / NaBH₄ / toluene; methanol / 1 h / -78 - 20 °C

8.1: DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

9.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

10.1: 4.90 g / Cs₂CO₃; PhSH / acetonitrile / 1 h / 20 °C

11.1: m-CPBA / CH₂Cl₂ / 0.5 h / 20 °C

12.1: 12 h / 20 °C

With pyridine; dmap; oxalyl dichloride; N,N-dimethylammonium chloride; diisobutylaluminium hydride; caesium carbonate; dimethyl sulfoxide; thiophenol; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic anhydride; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile; benzene; 2.1: Swern oxidation / 4.1: Michael addition;
DOI:10.1021/jo049862z