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

Base Information

• Chemical Name: 2-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethanol
• CAS No.: 138061-61-7
• Molecular Formula: C₂₂H₂₈O₅
• Molecular Weight: 372.461
• Mol file: 138061-61-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about 2-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethanol 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%

((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-acetic acid methyl ester → 2-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethanol (138061-61-7)

Guidance literature:

With lithium aluminium tetrahydride; 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 → 2-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethanol (138061-61-7)

Guidance literature:

Multi-step reaction with 2 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

With lithium aluminium tetrahydride; 3 A molecular sieve; 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 → 2-((3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethanol (138061-61-7)

Guidance literature:

Multi-step reaction with 3 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

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:

[(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:

(2R,3R,4R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-4-ol

(2R,3R,4S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-4-ol

(2R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-2-methylsulfanyl-tetrahydro-pyran-4-ol

(2R,4S,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-2-methylsulfanyl-tetrahydro-pyran-4-ol