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

Base Information

• Chemical Name: (2S,3R,4S,5R)-3,4-Bis-benzyloxy-5-(2-iodo-ethyl)-2-methoxy-tetrahydro-pyran
• CAS No.: 138607-82-6
• Molecular Formula: C₂₂H₂₇IO₄
• Molecular Weight: 482.358
• Mol file: 138607-82-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (2S,3R,4S,5R)-3,4-Bis-benzyloxy-5-(2-iodo-ethyl)-2-methoxy-tetrahydro-pyran 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: 94.0%

Methanesulfonic acid 2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl)-ethyl ester (138607-81-5) → (2S,3R,4S,5R)-3,4-Bis-benzyloxy-5-(2-iodo-ethyl)-2-methoxy-tetrahydro-pyran (138607-82-6)

Guidance literature:

With sodium hydrogencarbonate; sodium iodide; In acetone;

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 → (2S,3R,4S,5R)-3,4-Bis-benzyloxy-5-(2-iodo-ethyl)-2-methoxy-tetrahydro-pyran (138607-82-6)

Guidance literature:

Multi-step reaction with 4 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

4: 94 percent / NaI, NaHCO₃ / acetone

With lithium aluminium tetrahydride; 3 A molecular sieve; sodium hydrogencarbonate; triethylamine; sodium iodide; RhCl(PPh₃)3; In diethyl ether; acetone; 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 → (2S,3R,4S,5R)-3,4-Bis-benzyloxy-5-(2-iodo-ethyl)-2-methoxy-tetrahydro-pyran (138607-82-6)

Guidance literature:

Multi-step reaction with 5 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

5: 94 percent / NaI, NaHCO₃ / acetone

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

DOI:10.1021/jo00028a017

upstream raw materials:

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

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

[(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