Methanesulfonic acid (1R,2S,3R,4S)-2,3,4-tris-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-5-methanesulfonyloxy-pentyl ester

Base Information

• Chemical Name: Methanesulfonic acid (1R,2S,3R,4S)-2,3,4-tris-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-5-methanesulfonyloxy-pentyl ester
• CAS No.: 441310-83-4
• Molecular Formula: C₄₅H₅₄O₁₀S₂Si
• Molecular Weight: 847.135
• Mol file: 441310-83-4.mol

Synonyms:Methanesulfonic acid (1R,2S,3R,4S)-2,3,4-tris-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-5-methanesulfonyloxy-pentyl ester

Chemical Property of Methanesulfonic acid (1R,2S,3R,4S)-2,3,4-tris-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-5-methanesulfonyloxy-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (1R,2S,3R,4S)-2,3,4-tris-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-5-methanesulfonyloxy-pentyl ester

There total 8 articles about Methanesulfonic acid (1R,2S,3R,4S)-2,3,4-tris-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-5-methanesulfonyloxy-pentyl 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: 80.0%

methanesulfonyl chloride (124-63-0) + (2S,3R,4R,5R)-2,3,4-Tris-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexane-1,5-diol (441310-82-3) → Methanesulfonic acid (1R,2S,3R,4S)-2,3,4-tris-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-5-methanesulfonyloxy-pentyl ester (441310-83-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at -15 ℃; for 3h;

DOI:10.1016/S0040-4039(02)00250-2

Reference yield:

benzyl bromide (100-39-0) → Methanesulfonic acid (1R,2S,3R,4S)-2,3,4-tris-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-5-methanesulfonyloxy-pentyl ester (441310-83-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / NaH; 18-crown-6 / tetrahydrofuran / 19 h / 70 °C

2: 70 percent / NBS / acetonitrile; H₂O / 2 h

3: 92 percent / NaBH₄ / ethanol / 20 h

4: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / -15 °C

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; 18-crown-6 ether; sodium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(02)00250-2

Reference yield:

pent-4-enyl α,β-D-glucopyranoside (182074-52-8) → Methanesulfonic acid (1R,2S,3R,4S)-2,3,4-tris-benzyloxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-5-methanesulfonyloxy-pentyl ester (441310-83-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / DBU / tetrahydrofuran / 22 h

2: 85 percent / NaH; 18-crown-6 / tetrahydrofuran / 19 h / 70 °C

3: 70 percent / NBS / acetonitrile; H₂O / 2 h

4: 92 percent / NaBH₄ / ethanol / 20 h

5: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / -15 °C

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; 18-crown-6 ether; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(02)00250-2

upstream raw materials:

methanesulfonyl chloride

(2S,3R,4R,5R)-2,3,4-Tris-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexane-1,5-diol

benzyl bromide

pent-4-enyl α,β-D-glucopyranoside

Downstream raw materials:

2-[(2S,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylamine

(2S,3R,4R,5S)-1-Allyl-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidine

[2-((2S,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-hydroxymethyl-piperidin-1-yl)-ethyl]-carbamic acid (2S,3R,4R,5S)-1-(2-amino-ethyl)-3,4,5-tris-benzyloxy-piperidin-2-ylmethyl ester

4-(3-Methoxy-4-{2-[(2S,3R,4R,5S)-3,4,5-tris-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-piperidin-1-yl]-ethylcarbamoyloxymethyl}-phenoxy)-butyric acid methyl ester