Methanesulfonic acid 2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethyl ester

Base Information

• Chemical Name: Methanesulfonic acid 2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethyl ester
• CAS No.: 138607-81-5
• Molecular Formula: C₂₃H₃₀O₇S
• Molecular Weight: 450.553
• Mol file: 138607-81-5.mol

Synonyms:Methanesulfonic acid 2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethyl ester

Chemical Property of Methanesulfonic acid 2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid 2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethyl ester

There total 6 articles about Methanesulfonic acid 2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-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: 95.0%

2-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethanol (138061-61-7) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid 2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethyl ester (138607-81-5)

Guidance literature:

With triethylamine; In diethyl ether; at 0 ℃;

DOI:10.1021/jo00028a017

Reference yield:

((2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-2-formyl-6-methoxy-tetrahydro-pyran-3-yl)-acetic acid methyl ester → Methanesulfonic acid 2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethyl ester (138607-81-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) 3 Angstroem molecular sieves / 2) RhCl(PPh₃)3 / toluene / 1) reflux, 30 min., 2) reflux, 6 h

2: 95 percent / LiAlH₄ / diethyl ether / 0 °C

3: 95 percent / Et₃N / diethyl ether / 0 °C

With lithium aluminium tetrahydride; 3 A molecular sieve; triethylamine; RhCl(PPh₃)3; In diethyl ether; toluene;

DOI:10.1021/jo00028a017

Reference yield:

((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-acetic acid methyl ester → Methanesulfonic acid 2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethyl ester (138607-81-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) (COCl)2, DMSO, 2) Et₃N

2: 1) 3 Angstroem molecular sieves / 2) RhCl(PPh₃)3 / toluene / 1) reflux, 30 min., 2) reflux, 6 h

3: 95 percent / LiAlH₄ / diethyl ether / 0 °C

4: 95 percent / Et₃N / diethyl ether / 0 °C

With lithium aluminium tetrahydride; oxalyl dichloride; 3 A molecular sieve; dimethyl sulfoxide; triethylamine; RhCl(PPh₃)3; In diethyl ether; toluene;

DOI:10.1021/jo00028a017

upstream raw materials:

2-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethanol

methanesulfonyl chloride

[(2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl]-acetic acid methyl ester

Downstream raw materials:

(3S,4S,5R)-4,5-Bis-benzyloxy-1-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-pentan-2-one

(2S,3R,4S,5R)-3,4-Bis-benzyloxy-5-(2-iodo-ethyl)-2-methoxy-tetrahydro-pyran