benzyl (9S,8R,7R,6R,2Z,1R)-[10-benzyloxy-6,8-bis-(tert-butyl-dimethyl-silanyloxy)-7,9-dimethyl-1-propyl-dec-2-enyl]-carbamate

Base Information

Chemical Name:benzyl (9S,8R,7R,6R,2Z,1R)-[10-benzyloxy-6,8-bis-(tert-butyl-dimethyl-silanyloxy)-7,9-dimethyl-1-propyl-dec-2-enyl]-carbamate
CAS No.:883559-71-5
Molecular Formula:C₄₂H₇₁NO₅Si₂
Molecular Weight:726.2
Hs Code.:

Synonyms:benzyl (9S,8R,7R,6R,2Z,1R)-[10-benzyloxy-6,8-bis-(tert-butyl-dimethyl-silanyloxy)-7,9-dimethyl-1-propyl-dec-2-enyl]-carbamate

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Chemical Property of benzyl (9S,8R,7R,6R,2Z,1R)-[10-benzyloxy-6,8-bis-(tert-butyl-dimethyl-silanyloxy)-7,9-dimethyl-1-propyl-dec-2-enyl]-carbamate

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Useful:

Technology Process of benzyl (9S,8R,7R,6R,2Z,1R)-[10-benzyloxy-6,8-bis-(tert-butyl-dimethyl-silanyloxy)-7,9-dimethyl-1-propyl-dec-2-enyl]-carbamate

There total 10 articles about benzyl (9S,8R,7R,6R,2Z,1R)-[10-benzyloxy-6,8-bis-(tert-butyl-dimethyl-silanyloxy)-7,9-dimethyl-1-propyl-dec-2-enyl]-carbamate 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: 69.0%

: 883559-78-2
benzyl (9R,8R,7R,6R,2Z,1R)-(10-benzyloxy-6,8-dihydroxy-7,9-dimethyl-1-propyl-dec-2-enyl)-carbamate

: 69739-34-0
t-butyldimethylsiyl triflate

: 883559-71-5
benzyl (9S,8R,7R,6R,2Z,1R)-[10-benzyloxy-6,8-bis-(tert-butyl-dimethyl-silanyloxy)-7,9-dimethyl-1-propyl-dec-2-enyl]-carbamate

Guidance literature:: With 2,6-dimethylpyridine; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1016/j.tet.2006.01.005

Reference yield:

: 883559-74-8
(R)-2-benzyloxycarbonylaminopentanal

: 883559-71-5
benzyl (9S,8R,7R,6R,2Z,1R)-[10-benzyloxy-6,8-bis-(tert-butyl-dimethyl-silanyloxy)-7,9-dimethyl-1-propyl-dec-2-enyl]-carbamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium bistrimethylsilylamide / tetrahydrofuran / 1 h / 0 °C

1.2: 78 percent / tetrahydrofuran / 1 h / 0 °C

2.1: 91 percent / DIBAL-H / toluene / 2 h / -78 °C

3.1: Et₃N; dicyclohexylboron chloride / hexane; diethyl ether / 2 h / 0 °C

3.2: diethyl ether / -78 - -20 °C

3.3: 85 percent / hydrogen peroxide / H₂O; diethyl ether; methanol / 3 h / 20 °C / pH 7

4.1: 78 percent / Me₄NBH(OAc)3; acetic acid / acetonitrile / 4 h / -15 °C

5.1: 69 percent / 2,6-lutidine / tetrahydrofuran / 4 h / 20 °C

With 2,6-dimethylpyridine; dicyclohexylboron chloride; sodium hexamethyldisilazane; diisobutylaluminium hydride; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; hexane; toluene; acetonitrile; 1.2: Wittig reaction;
DOI:10.1016/j.tet.2006.01.005

Reference yield:

: 883559-76-0
(4Z)-(6R)-6-benzyloxycarbonylaminonon-4-enal

: 883559-71-5
benzyl (9S,8R,7R,6R,2Z,1R)-[10-benzyloxy-6,8-bis-(tert-butyl-dimethyl-silanyloxy)-7,9-dimethyl-1-propyl-dec-2-enyl]-carbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: Et₃N; dicyclohexylboron chloride / hexane; diethyl ether / 2 h / 0 °C

1.2: diethyl ether / -78 - -20 °C

1.3: 85 percent / hydrogen peroxide / H₂O; diethyl ether; methanol / 3 h / 20 °C / pH 7

2.1: 78 percent / Me₄NBH(OAc)3; acetic acid / acetonitrile / 4 h / -15 °C

3.1: 69 percent / 2,6-lutidine / tetrahydrofuran / 4 h / 20 °C

With 2,6-dimethylpyridine; dicyclohexylboron chloride; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; hexane; acetonitrile;
DOI:10.1016/j.tet.2006.01.005