Toluene-4-sulfonic acid 2-[(R)-2-hydroxy-1-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-ethyl ester

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Chemical Name:Toluene-4-sulfonic acid 2-[(R)-2-hydroxy-1-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-ethyl ester
CAS No.:263916-93-4
Molecular Formula:C₁₈H₂₆O₉S
Molecular Weight:418.465
Hs Code.:

Synonyms:Toluene-4-sulfonic acid 2-[(R)-2-hydroxy-1-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-ethyl ester

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Chemical Property of Toluene-4-sulfonic acid 2-[(R)-2-hydroxy-1-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-ethyl ester

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Technology Process of Toluene-4-sulfonic acid 2-[(R)-2-hydroxy-1-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-ethyl ester

There total 5 articles about Toluene-4-sulfonic acid 2-[(R)-2-hydroxy-1-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-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:

: 263916-91-2
6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose

: 263916-93-4
Toluene-4-sulfonic acid 2-[(R)-2-hydroxy-1-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-ethyl ester

Guidance literature:: 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-(β-p-toluenesulfonyloxyethyl)-α-D-glucofuranose; With hydrogen; palladium on activated charcoal; In methanol;

With sodium methylate; In methanol; dichloromethane; at -10 ℃;
DOI:10.1080/07328300008544068

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 263916-93-4
Toluene-4-sulfonic acid 2-[(R)-2-hydroxy-1-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 62 percent / CH₂Cl₂; pyridine / 1 h / -78 °C

2.1: 82 percent / tris(dibenzylideneacetone)dipalladium; 1,4-bis-(diphenylphosphino)butane / tetrahydrofuran / 60 °C

3.1: O₃ / CH₂Cl₂; methanol / 0.5 h / -78 °C

3.2: 81 percent / NaBH₄ / CH₂Cl₂; methanol / -78 - 20 °C

4.1: 70 percent / CH₂Cl₂; pyridine / 20 °C

5.1: H₂ / 10 percent Pd/C / methanol

5.2: NaOMe / methanol; CH₂Cl₂ / -10 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; hydrogen; ozone; 1,4-di(diphenylphosphino)-butane; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; 1.1: Acetylation / 2.1: Alkylation / 3.1: Oxidation / 3.2: Reduction / 4.1: Tosylation / 5.1: Hydrogenolysis / 5.2: Deacetylation;
DOI:10.1080/07328300008544068

Reference yield:

: 177897-25-5
6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

: 263916-93-4
Toluene-4-sulfonic acid 2-[(R)-2-hydroxy-1-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 82 percent / tris(dibenzylideneacetone)dipalladium; 1,4-bis-(diphenylphosphino)butane / tetrahydrofuran / 60 °C

2.1: O₃ / CH₂Cl₂; methanol / 0.5 h / -78 °C

2.2: 81 percent / NaBH₄ / CH₂Cl₂; methanol / -78 - 20 °C

3.1: 70 percent / CH₂Cl₂; pyridine / 20 °C

4.1: H₂ / 10 percent Pd/C / methanol

4.2: NaOMe / methanol; CH₂Cl₂ / -10 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; hydrogen; ozone; 1,4-di(diphenylphosphino)-butane; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; 1.1: Alkylation / 2.1: Oxidation / 2.2: Reduction / 3.1: Tosylation / 4.1: Hydrogenolysis / 4.2: Deacetylation;
DOI:10.1080/07328300008544068