Methanesulfonic acid (1S,2R,3R)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-butyl ester

Base Information

• Chemical Name: Methanesulfonic acid (1S,2R,3R)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-butyl ester
• CAS No.: 258846-76-3
• Molecular Formula: C₂₈H₅₄O₆SSi₂
• Molecular Weight: 574.97

Synonyms:Methanesulfonic acid (1S,2R,3R)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-butyl ester

Chemical Property of Methanesulfonic acid (1S,2R,3R)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (1S,2R,3R)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-butyl ester

There total 10 articles about Methanesulfonic acid (1S,2R,3R)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-butyl 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: 97.7%

methanesulfonyl chloride (124-63-0) + (2S,3S,4S,5R)-4-Benzyloxymethyl-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hexan-3-ol (258846-65-0) → Methanesulfonic acid (1S,2R,3R)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-butyl ester (258846-76-3)

Guidance literature:

In pyridine;

DOI:10.1039/a907922j

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → Methanesulfonic acid (1S,2R,3R)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-butyl ester (258846-76-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 70 percent / HMPA; LDA / -78 °C

2: 90 percent / imidazole / dimethylformamide

3: 86 percent / DIBAL-H / diethyl ether / -78 °C

4: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -65 - -55 °C

5: LiCl; i-Pr₂NEt / acetonitrile

6: 95 percent / DIBAL-H / diethyl ether / -78 °C

7: 76.5 percent / Ti(O-i-Pr)4; D-(-)-diisopropyl tartrate; t-BuOOH

8: 72.4 percent / diethyl ether / -20 - 0 °C

9: 84.4 percent / Et₃N; DMAP / CH₂Cl₂

10: 97.7 percent / pyridine

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; oxalyl dichloride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide; In pyridine; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Alkylation / 2: Substitution / 3: Reduction / 4: Oxidation / 5: Condensation / 6: Reduction / 7: Epoxidation / 8: Ring cleavage / 9: Substitution / 10: Mesylation;

DOI:10.1039/a907922j

Reference yield:

(2R,3R)-methyl 2-[(benzyloxy)methyl]-3-hydroxybutyrate (107441-54-3) → Methanesulfonic acid (1S,2R,3R)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-butyl ester (258846-76-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / imidazole / dimethylformamide

2: 86 percent / DIBAL-H / diethyl ether / -78 °C

3: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -65 - -55 °C

4: LiCl; i-Pr₂NEt / acetonitrile

5: 95 percent / DIBAL-H / diethyl ether / -78 °C

6: 76.5 percent / Ti(O-i-Pr)4; D-(-)-diisopropyl tartrate; t-BuOOH

7: 72.4 percent / diethyl ether / -20 - 0 °C

8: 84.4 percent / Et₃N; DMAP / CH₂Cl₂

9: 97.7 percent / pyridine

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; oxalyl dichloride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In pyridine; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Reduction / 3: Oxidation / 4: Condensation / 5: Reduction / 6: Epoxidation / 7: Ring cleavage / 8: Substitution / 9: Mesylation;

DOI:10.1039/a907922j

upstream raw materials:

methanesulfonyl chloride

(2S,3S,4S,5R)-4-Benzyloxymethyl-1,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hexan-3-ol

Benzyloxymethyl chloride

(2R,3R)-methyl 2-[(benzyloxy)methyl]-3-hydroxybutyrate

Downstream raw materials:

{(2R,3S,4R)-3-Azido-5-(tert-butyl-dimethyl-silanyloxy)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-pentyloxymethyl}-benzene

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