[(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

Base Information

Chemical Name:[(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester
CAS No.:1262295-40-8
Molecular Formula:C₂₂H₃₄O₅
Molecular Weight:378.509
Hs Code.:

Synonyms:[(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

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Chemical Property of [(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

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Technology Process of [(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

There total 14 articles about [(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid 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: 83.0%

: 1262295-41-9
(E)-(S)-5-benzyloxy-6-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-4,4-dimethyl-hex-2-enoic acid ethyl ester

: 1262295-40-8
[(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

Guidance literature:: With toluene-4-sulfonic acid; In chloroform; for 20h; optical yield given as %de; stereoselective reaction; Reflux; Inert atmosphere;
DOI:10.1021/jo101782q

Reference yield:

: 1262295-45-3
(3R,5R,7S)-7-benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-8,8-dimethyl-nonane-3,5-diol

: 1262295-40-8
[(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 - 60 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

4.1: toluene / 48 h / Reflux; Inert atmosphere

5.1: toluene-4-sulfonic acid / chloroform / 20 h / Reflux; Inert atmosphere

With oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; chloroform; toluene; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.1: Horner-Wittig reaction / 5.1: oxa-Michael cyclization;
DOI:10.1021/jo101782q

Reference yield:

: 1262295-47-5
(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butan-1-ol

: 1262295-40-8
[(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: toluene / 48 h / Reflux; Inert atmosphere

3.1: toluene-4-sulfonic acid / chloroform / 20 h / Reflux; Inert atmosphere

With oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; In dichloromethane; chloroform; toluene; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Horner-Wittig reaction / 3.1: oxa-Michael cyclization;
DOI:10.1021/jo101782q