(2R)-1-(3aR,5R,6S,6aR)-1-(6-allyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl 4-methyl benzenesulfonate

Base Information

Chemical Name:(2R)-1-(3aR,5R,6S,6aR)-1-(6-allyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl 4-methyl benzenesulfonate
CAS No.:134311-87-8
Molecular Formula:C₁₉H₂₆O₈S
Molecular Weight:414.477
Hs Code.:

Synonyms:(2R)-1-(3aR,5R,6S,6aR)-1-(6-allyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl 4-methyl benzenesulfonate

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Chemical Property of (2R)-1-(3aR,5R,6S,6aR)-1-(6-allyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl 4-methyl benzenesulfonate

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Technology Process of (2R)-1-(3aR,5R,6S,6aR)-1-(6-allyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl 4-methyl benzenesulfonate

There total 5 articles about (2R)-1-(3aR,5R,6S,6aR)-1-(6-allyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl 4-methyl benzenesulfonate 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: 89.0%

: 91882-92-7
3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose

: 98-59-9
p-toluenesulfonyl chloride

: 134311-87-8
(2R)-1-(3aR,5R,6S,6aR)-1-(6-allyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl 4-methyl benzenesulfonate

Guidance literature:: With dmap; In pyridine; dichloromethane; for 96h; Ambient temperature;

Reference yield:

: 20316-77-2
(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

: 134311-87-8
(2R)-1-(3aR,5R,6S,6aR)-1-(6-allyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl 4-methyl benzenesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1: 46 percent / toluenesulfonic acid monohydrate / methanol / 5 h / 20 °C

2: pyridine / 0 - 20 °C

With toluene-4-sulfonic acid; In pyridine; methanol;
DOI:10.1021/ol027288c

Reference yield:

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 134311-87-8
(2R)-1-(3aR,5R,6S,6aR)-1-(6-allyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl 4-methyl benzenesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / NaH; TBAI / tetrahydrofuran; various solvent(s) / 24 h

2: 46 percent / toluenesulfonic acid monohydrate / methanol / 5 h / 20 °C

3: pyridine / 0 - 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol;
DOI:10.1021/ol027288c