(2R,3S,4E,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,8-dimethoxy-11-(3-nitro-2,5,6-trimethoxy-phenyl)-4,6,10-trimethyl-undec-4-enoic acid methyl ester

Base Information

Chemical Name:(2R,3S,4E,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,8-dimethoxy-11-(3-nitro-2,5,6-trimethoxy-phenyl)-4,6,10-trimethyl-undec-4-enoic acid methyl ester
CAS No.:474411-01-3
Molecular Formula:C₃₂H₅₅NO₁₁Si
Molecular Weight:657.874
Hs Code.:

(2R,3S,4E,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,8-dimethoxy-11-(3-nitro-2,5,6-trimethoxy-phenyl)-4,6,10-trimethyl-undec-4-enoic acid methyl ester

Synonyms:(2R,3S,4E,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,8-dimethoxy-11-(3-nitro-2,5,6-trimethoxy-phenyl)-4,6,10-trimethyl-undec-4-enoic acid methyl ester

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Chemical Property of (2R,3S,4E,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,8-dimethoxy-11-(3-nitro-2,5,6-trimethoxy-phenyl)-4,6,10-trimethyl-undec-4-enoic acid methyl ester

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Technology Process of (2R,3S,4E,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,8-dimethoxy-11-(3-nitro-2,5,6-trimethoxy-phenyl)-4,6,10-trimethyl-undec-4-enoic acid methyl ester

There total 17 articles about (2R,3S,4E,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,8-dimethoxy-11-(3-nitro-2,5,6-trimethoxy-phenyl)-4,6,10-trimethyl-undec-4-enoic acid methyl 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:

: 474411-09-1
(3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-6-methyl-7-(5-nitro-2,3,6-trimethoxy-phenyl)-heptan-2-one

: 474411-01-3
(2R,3S,4E,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,8-dimethoxy-11-(3-nitro-2,5,6-trimethoxy-phenyl)-4,6,10-trimethyl-undec-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: NaHMDS / diethyl ether / 1 h / 0 - 20 °C

1.2: 98 percent / diethyl ether / 2 h / 20 °C

2.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 °C

3.1: BH₃*THF / tetrahydrofuran / 2.25 h / -5 °C

3.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 2 h / 0 - 20 °C

4.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

5.1: 80 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 °C

6.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 °C

7.1: 93 percent / toluene / 7 h / 90 °C

8.1: 86 percent / DIBAL-H / tetrahydrofuran; toluene / 4 h / -78 °C

9.1: 89 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C

10.1: Et₃N; c-Hex₂BOTf / CH₂Cl₂ / 2.5 h / -78 °C

10.2: 92 percent / CH₂Cl₂ / 3 h / -78 °C

11.1: aq. LiOH / tetrahydrofuran / 0 - 20 °C

12.1: 0.217 g / benzene; methanol; hexane / 2 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; borane-THF; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; benzene; 1.2: Wittig reaction;
DOI:10.1021/jo034870l

Reference yield:

: 474410-96-3
(3R,4S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-4-methoxy-7-(5-nitro-2,3,6-trimethoxy-phenyl)-hept-1-ene

: 474411-01-3
(2R,3S,4E,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,8-dimethoxy-11-(3-nitro-2,5,6-trimethoxy-phenyl)-4,6,10-trimethyl-undec-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 °C

2.1: BH₃*THF / tetrahydrofuran / 2.25 h / -5 °C

2.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 2 h / 0 - 20 °C

3.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

4.1: 80 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 °C

5.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 °C

6.1: 93 percent / toluene / 7 h / 90 °C

7.1: 86 percent / DIBAL-H / tetrahydrofuran; toluene / 4 h / -78 °C

8.1: 89 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C

9.1: Et₃N; c-Hex₂BOTf / CH₂Cl₂ / 2.5 h / -78 °C

9.2: 92 percent / CH₂Cl₂ / 3 h / -78 °C

10.1: aq. LiOH / tetrahydrofuran / 0 - 20 °C

11.1: 0.217 g / benzene; methanol; hexane / 2 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; borane-THF; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen fluoride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; acetonitrile; benzene;
DOI:10.1021/jo034870l

Reference yield:

: 474410-99-6
(2E,4S,5R,6S,8R)-5-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-9-(3-nitro-2,5,6-trimethoxy-phenyl)-2,4,8-trimethyl-non-2-enal

: 474411-01-3
(2R,3S,4E,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,8-dimethoxy-11-(3-nitro-2,5,6-trimethoxy-phenyl)-4,6,10-trimethyl-undec-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: Et₃N; c-Hex₂BOTf / CH₂Cl₂ / 2.5 h / -78 °C

1.2: 92 percent / CH₂Cl₂ / 3 h / -78 °C

2.1: aq. LiOH / tetrahydrofuran / 0 - 20 °C

3.1: 0.217 g / benzene; methanol; hexane / 2 h / 20 °C

With lithium hydroxide; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
DOI:10.1021/jo034870l