(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
Hs Code.:

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

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

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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%

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

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

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

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

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

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

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