2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester
CAS No.:164215-39-8
Molecular Formula:C₄₈H₈₄O₁₁Si₂
Molecular Weight:893.359
Hs Code.:

2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Synonyms:2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

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Technology Process of 2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

There total 27 articles about 2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-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: 99.0%

: 164215-38-7
2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

: 164215-39-8
2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Guidance literature:: With hydrogen; palladium dihydroxide; Lindlar's catalyst; calcium carbonate;
DOI:10.1021/ja00102a074

Reference yield:

: 171189-78-9
(S)-2-[(R)-Benzyloxy-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-methyl]-4-trimethylsilanyl-but-3-yne-1,2-diol

: 164215-39-8
2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 78 percent / methanolic K₂CO₃ / 8 h / 23 °C

2: Et₃N, 4-DMAP / CH₂Cl₂ / 12 h / 23 °C

3: Et₃N, 4-DMAP / CH₂Cl₂ / 0.5 h / 23 °C

4: 1.) n-BuLi, 2.) LiBr / 1.) THF, hexane, -45 deg C, 45 min, 2.) THF, hexane, -45 deg C, 10 min

5: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 23 °C

6: 60 percent / 2O>2 / H₂O; tetrahydrofuran / 336 h / 65 °C

7: 93 percent / n-Bu₄NF / tetrahydrofuran / 0.75 h

8: (DHQD)2PHAL, 4-methylmorpholine N-oxide, CH₃SO₂NH₂, aq. OsO₄ / acetone; 2-methyl-propan-2-ol / 12 h / 23 °C

9: 86 percent / 12N aq. HCl / methanol / 2 h / 23 °C

10: Et₃N, 4-DMAP / CH₂Cl₂ / 46 h / 23 °C

11: 97 percent / 4-DMAP / 1,2-dichloro-ethane / 8 h / 55 °C

12: 99 percent / H₂ / 20percent Pd(OH)2/C, 5percent Pd/CaCO₃ / ethanol / 168 h / 23 °C / 760 Torr

With hydrogenchloride; dmap; osmium(VIII) oxide; n-butyllithium; methanesulfonamide; 2; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; lithium bromide; palladium dihydroxide; Lindlar's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetone; tert-butyl alcohol;
DOI:10.1021/ja00136a008

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 164215-39-8
2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N, 4-DMAP / CH₂Cl₂ / 46 h / 23 °C

2: 97 percent / 4-DMAP / 1,2-dichloro-ethane / 8 h / 55 °C

3: 99 percent / H₂ / 20percent Pd(OH)2/C, 5percent Pd/CaCO₃ / ethanol / 168 h / 23 °C / 760 Torr

With dmap; hydrogen; triethylamine; palladium dihydroxide; Lindlar's catalyst; In ethanol; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/ja00136a008