{(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: {(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 289667-08-9
• Molecular Formula: C₃₅H₅₅NO₈Si₂
• Molecular Weight: 673.995
• Mol file: 289667-08-9.mol

Synonyms:{(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl ester

Chemical Property of {(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl ester

There total 6 articles about {(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl 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: 100.0%

tert-butylchlorodiphenylsilane (58479-61-1) + [(4S,4aS,6R,8S,8aR)-6-((S)-2,3-Dihydroxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester (289667-07-8) → {(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl ester (289667-08-9)

Guidance literature:

With dmap; triethylamine;

DOI:10.1021/ol000072v

Reference yield:

(S)-4-((4R,4aR,6R,8S,8aR)-4-Hydroxymethyl-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl)-[1,3]dioxolan-2-one (289667-01-2) → {(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl ester (289667-08-9)

Guidance literature:

Multi-step reaction with 4 steps

1: Jones reagent

2: (PhO)2P(O)N₃; Et₃N; 4 Angstroem molecular sieves / 65 °C

3: 76 percent / LiOH*H₂O / methanol

4: 100 percent / DMAP Et₃N

With dmap; lithium hydroxide; jones reagent; 4 A molecular sieve; diphenyl phosphoryl azide; triethylamine; In methanol; 1: Oxidation / 2: Curtius rearrangement / 3: Hydrolysis / 4: silylation;

DOI:10.1021/ol000072v

Reference yield:

[(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester (168072-64-8) → {(4S,4aS,6R,8S,8aR)-6-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl ester (289667-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / LiOH*H₂O / methanol

2: 100 percent / DMAP Et₃N

With dmap; lithium hydroxide; triethylamine; In methanol; 1: Hydrolysis / 2: silylation;

DOI:10.1021/ol000072v

upstream raw materials:

tert-butylchlorodiphenylsilane

[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-Dihydroxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester

(S)-4-((4R,4aR,6R,8S,8aR)-4-Hydroxymethyl-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl)-[1,3]dioxolan-2-one

[(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester