{(2S,4R,6S)-6-[2-(benzyloxy)ethyl]tetrahydro-4-hydroxy-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

Base Information

Chemical Name:{(2S,4R,6S)-6-[2-(benzyloxy)ethyl]tetrahydro-4-hydroxy-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate
CAS No.:1173106-14-3
Molecular Formula:C₂₂H₂₈O₆S
Molecular Weight:420.527
Hs Code.:

Synonyms:{(2S,4R,6S)-6-[2-(benzyloxy)ethyl]tetrahydro-4-hydroxy-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

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Chemical Property of {(2S,4R,6S)-6-[2-(benzyloxy)ethyl]tetrahydro-4-hydroxy-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

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Technology Process of {(2S,4R,6S)-6-[2-(benzyloxy)ethyl]tetrahydro-4-hydroxy-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

There total 11 articles about {(2S,4R,6S)-6-[2-(benzyloxy)ethyl]tetrahydro-4-hydroxy-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate 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%

: 1173106-13-2
(2S,4R,6S)-2-[2-(benzyloxy)ethyl]tetrahydro-6-(hydroxymethyl)-2H-pyran-4-ol

: 98-59-9
p-toluenesulfonyl chloride

: 1173106-14-3
{(2S,4R,6S)-6-[2-(benzyloxy)ethyl]tetrahydro-4-hydroxy-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; for 5h;
DOI:10.1002/hlca.200800355

Reference yield: 73.0%

: {(2S,6S)-6-[2-(benzyloxy)ethyl]-4-oxotetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

: 1173106-14-3
{(2S,4R,6S)-6-[2-(benzyloxy)ethyl]tetrahydro-4-hydroxy-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

: {(2S,4S,6S)-6-[2-(benzyloxy)ethyl]-4-hydroxytetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 ℃; for 1h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/acs.joc.5b01323

Reference yield:

: 19790-60-4
3-Benzyloxypropanal

: 118629-75-7
(S)-2-hydroxypent-4-en-1-yl 4-methylbenzenesulfonate

: 1173106-14-3
{(2S,4R,6S)-6-[2-(benzyloxy)ethyl]tetrahydro-4-hydroxy-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

: {(2S,4S,6S)-6-[2-(benzyloxy)ethyl]-4-hydroxytetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

Guidance literature:: 3-Benzyloxypropanal; (S)-2-hydroxypent-4-en-1-yl 4-methylbenzenesulfonate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

With sodium hydrogencarbonate; triethylamine; In dichloromethane; at 20 ℃; for 3h; pH=> 7; Overall yield = 70 %; Overall yield = 718 mg; Inert atmosphere;
DOI:10.1021/acs.joc.5b01323