(2R,3R,8S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-non-5-yn-3-ol

Base Information

• Chemical Name: (2R,3R,8S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-non-5-yn-3-ol
• CAS No.: 313677-46-2
• Molecular Formula: C₃₆H₅₈O₆Si₂
• Molecular Weight: 643.024
• Mol file: 313677-46-2.mol

Synonyms:(2R,3R,8S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-non-5-yn-3-ol

Chemical Property of (2R,3R,8S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-non-5-yn-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,8S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-non-5-yn-3-ol

There total 4 articles about (2R,3R,8S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-non-5-yn-3-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: 60.0%

(S)-5-Benzyloxy-4-tert-butyldimethylsiloxy-1-pentyne (124662-63-1) + tert-Butyl-[(R)-2-(4-methoxy-benzyloxy)-1-(R)-oxiranyl-ethoxy]-dimethyl-silane (313677-45-1) → (2R,3R,8S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-non-5-yn-3-ol (313677-46-2)

Guidance literature:

With n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)01344-7

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3R,8S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-non-5-yn-3-ol (313677-46-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaH / tetrahydrofuran

2: 60 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

With n-butyllithium; boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; 1: Etherification / 2: Alkylation;

DOI:10.1016/S0040-4039(00)01344-7

Reference yield:

(S)-5-Benzyloxy-4-hydroxy-1-pentyne (124662-61-9) → (2R,3R,8S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-non-5-yn-3-ol (313677-46-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaH / tetrahydrofuran

2: 60 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

With n-butyllithium; boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; 1: Etherification / 2: Alkylation;

DOI:10.1016/S0040-4039(00)01344-7

upstream raw materials:

(S)-5-Benzyloxy-4-tert-butyldimethylsiloxy-1-pentyne

tert-Butyl-[(R)-2-(4-methoxy-benzyloxy)-1-(R)-oxiranyl-ethoxy]-dimethyl-silane

tert-butyldimethylsilyl chloride

(S)-5-Benzyloxy-4-hydroxy-1-pentyne

Downstream raw materials:

4-Nitro-benzoic acid (R)-1-benzyloxymethyl-5-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-pentyl ester

(R)-1-Benzyloxy-6-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-hexan-2-ol

(S)-1-Benzyloxy-6-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-hexan-2-ol

(2R,3R,8S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-nonan-3-ol