2,2-Dimethyl-propionic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester
• CAS No.: 186448-87-3
• Molecular Formula: C₄₅H₇₈O₇S₂Si
• Molecular Weight: 823.328
• Mol file: 186448-87-3.mol

Synonyms:2,2-Dimethyl-propionic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester

There total 20 articles about 2,2-Dimethyl-propionic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl 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: 87.0%

pivaloyl chloride (3282-30-2) + (E)-(2R,5R)-5-{2-[(2S,3R)-2-(4-Methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-ene-1,2-diol (186448-80-6) → 2,2-Dimethyl-propionic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester (186448-87-3)

Guidance literature:

With dmap;

DOI:10.1016/S0040-4039(00)73279-5 DOI:10.1021/ja963066w

Reference yield:

(1R,2R,4R)-4-<(phenylsulfonyl)methyl>-2-methoxy-1-<oxy>cyclohexane (127258-23-5) → 2,2-Dimethyl-propionic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester (186448-87-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-BuLi, 2.) BF₃*Et₂O, 3.) Na₂HPO₄, 4.) Na(Hg)

2: 92 percent / Et₃N

3: 87 percent / NaH / hexamethylphosphoric acid triamide / 6 h / Ambient temperature

4: 78 percent / LiI, BF₃*OEt₂ / diethyl ether / -78 °C

5: 84 percent / BF₃*Et₂O / CH₂Cl₂ / -78 °C

6: 87 percent / t-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C

7: 73 percent / camphorsulfonic acid / methanol / 2 h / Ambient temperature

8: 87 percent / DMAP

With dmap; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tert.-butyl lithium; sodium hydride; triethylamine; lithium iodide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;

DOI:10.1021/ja963066w

Reference yield:

Triisopropyl-[(1R,2R,4S)-2-methoxy-4-((R)-(R)-2-oxiranyl-propyl)-cyclohexyloxy]-silane (143619-00-5) → 2,2-Dimethyl-propionic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester (186448-87-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / LiI, BF₃*OEt₂ / diethyl ether / -78 °C

2: 84 percent / BF₃*Et₂O / CH₂Cl₂ / -78 °C

3: 87 percent / t-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C

4: 73 percent / camphorsulfonic acid / methanol / 2 h / Ambient temperature

5: 87 percent / DMAP

With dmap; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tert.-butyl lithium; lithium iodide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;

DOI:10.1021/ja963066w

upstream raw materials:

pivaloyl chloride

(E)-(2R,5R)-5-{2-[(2S,3R)-2-(4-Methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-ene-1,2-diol

(1R,2R,4R)-4-<(phenylsulfonyl)methyl>-2-methoxy-1-<oxy>cyclohexane

O-(4-methoxybenzyl)-trichloroacetimidate

Downstream raw materials:

2,2-Dimethyl-propionic acid (E)-(2R,5R)-2-(tert-butyl-dimethyl-silanyloxy)-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester

(E)-(2R,3S,6R,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-10-hydroxy-3-(4-methoxy-benzyloxy)-1-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,6,8-trimethyl-dec-7-en-5-one

(E)-(2R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-en-1-ol