(2Z,6E)-(4S,5S,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,9,10,13-tetramethoxy-6,8,12-trimethyl-trideca-2,6-dien-1-ol

Base Information

Chemical Name:(2Z,6E)-(4S,5S,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,9,10,13-tetramethoxy-6,8,12-trimethyl-trideca-2,6-dien-1-ol
CAS No.:145798-95-4
Molecular Formula:C₅₃H₇₅NO₈Si
Molecular Weight:882.266
Hs Code.:

(2Z,6E)-(4S,5S,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,9,10,13-tetramethoxy-6,8,12-trimethyl-trideca-2,6-dien-1-ol

Synonyms:(2Z,6E)-(4S,5S,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,9,10,13-tetramethoxy-6,8,12-trimethyl-trideca-2,6-dien-1-ol

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Chemical Property of (2Z,6E)-(4S,5S,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,9,10,13-tetramethoxy-6,8,12-trimethyl-trideca-2,6-dien-1-ol

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Technology Process of (2Z,6E)-(4S,5S,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,9,10,13-tetramethoxy-6,8,12-trimethyl-trideca-2,6-dien-1-ol

There total 17 articles about (2Z,6E)-(4S,5S,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,9,10,13-tetramethoxy-6,8,12-trimethyl-trideca-2,6-dien-1-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: 89.0%

: 145798-88-5
methyl (2Z,4S,5S,6E,8S,9R,10S,12S,13R)-5-<(t-butyldimethylsilyl)oxy>-13-<2,5-dimethoxy-3-<(triphenylmethyl)amino>phenyl>-4,9,10,13-tetramethoxy-6,8,12-trimethyl-2,6-tridecadienoate

: 145798-95-4
(2Z,6E)-(4S,5S,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,9,10,13-tetramethoxy-6,8,12-trimethyl-trideca-2,6-dien-1-ol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 1h;
DOI:10.1246/bcsj.65.2974

Reference yield:

: 145798-85-2
(2R,3R,4S,6S)-3,4-Dimethoxy-7-(4-methoxy-benzyloxy)-2,6-dimethyl-heptanal

: 145798-95-4
(2Z,6E)-(4S,5S,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,9,10,13-tetramethoxy-6,8,12-trimethyl-trideca-2,6-dien-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) s-butyllithium / 1.) THF, cyclohexane, RT, 0.5 h, 2.) THF, cyclohexane, from -78 deg C to -20 deg C, 4.5 h

2: 1.) s-BuLi, 2.) (+)-B-methoxydiisopinocampheylborane, 3.) BF₃*Et₂O

3: 91 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

4: 97 percent / DDQ / CH₂Cl₂; H₂O / 1 h / Ambient temperature

5: 88 percent / oxalyl dichloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

6: 1.) butyllithium / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, -78 deg C, 2 h

7: 100 percent / NaH / dimethylformamide / 6.5 h / 0 °C

8: 76 percent / OsO₄-NaIO₄, phosphate buffer / tetrahydrofuran / 16 h / Ambient temperature

9: 1.) 18-crown-6, potassium bis(trimethylsilyl)amide / 1.) THF, toluene, -78 deg C, 0.5 h, 2.) THF, toluene, -78 deg C, 1 h

10: 89 percent / DIBAL / toluene / 1 h / -78 °C

With (+)-Ipc₂BOMe; 1H-imidazole; sodium periodate; osmium(VIII) oxide; n-butyllithium; phosphate buffer; oxalyl dichloride; 18-crown-6 ether; boron trifluoride diethyl etherate; sec.-butyllithium; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1246/bcsj.65.2974

Reference yield:

: 137788-15-9
(2E,4S,5R,6S,8S)-5,6-dimethoxy-9-<(4-methoxybenzyl)oxy>-2,4,8-trimethyl-2-nonenal

: 145798-95-4
(2Z,6E)-(4S,5S,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[2,5-dimethoxy-3-(trityl-amino)-phenyl]-4,9,10,13-tetramethoxy-6,8,12-trimethyl-trideca-2,6-dien-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) s-BuLi, 2.) (+)-B-methoxydiisopinocampheylborane, 3.) BF₃*Et₂O

2: 91 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

3: 97 percent / DDQ / CH₂Cl₂; H₂O / 1 h / Ambient temperature

4: 88 percent / oxalyl dichloride, DMSO / CH₂Cl₂ / 0.25 h / -78 °C

5: 1.) butyllithium / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, -78 deg C, 2 h

6: 100 percent / NaH / dimethylformamide / 6.5 h / 0 °C

7: 76 percent / OsO₄-NaIO₄, phosphate buffer / tetrahydrofuran / 16 h / Ambient temperature

8: 1.) 18-crown-6, potassium bis(trimethylsilyl)amide / 1.) THF, toluene, -78 deg C, 0.5 h, 2.) THF, toluene, -78 deg C, 1 h

9: 89 percent / DIBAL / toluene / 1 h / -78 °C

With (+)-Ipc₂BOMe; 1H-imidazole; sodium periodate; osmium(VIII) oxide; n-butyllithium; phosphate buffer; oxalyl dichloride; 18-crown-6 ether; boron trifluoride diethyl etherate; sec.-butyllithium; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1246/bcsj.65.2974