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

Base Information

• Chemical Name: Toluene-4-sulfonic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester
• CAS No.: 1054652-94-6
• Molecular Formula: C₁₆H₁₉NO₇S
• Molecular Weight: 369.395

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

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

Chemical Property:

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

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

1,2-O-isopropylidene-5-O-p-toluenesulfonyl-α-D-erythro-ketofuranos-3-ulose (20514-01-6) + sodium cyanide (143-33-9,25596-52-5) → Toluene-4-sulfonic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester (1054652-94-6)

Guidance literature:

With sodium hydrogencarbonate; In diethyl ether; water; at 20 ℃; for 4h;

DOI:10.1021/jo0609531

Reference yield:

1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose (6893-65-8,20513-95-5,20513-96-6,34981-06-1,40429-51-4,110349-61-6) → Toluene-4-sulfonic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester (1054652-94-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium dichromate; acetic anhydride / CH₂Cl₂ / Heating

2: sodium hydrogencarbonate / diethyl ether; H₂O / 4 h / 20 °C

With dipyridinium dichromate; acetic anhydride; sodium hydrogencarbonate; In diethyl ether; dichloromethane; water;

DOI:10.1021/jo0609531

Reference yield: 67.0%

Toluene-4-sulfonic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester (1054652-94-6) + methanesulfonyl chloride (124-63-0) → 3-C-cyano-1,2-O-isopropylidene-3-O-mesyl-5-O-tosyl-α-D-ribofuranose (911429-57-7)

Guidance literature:

With pyridine; at 5 ℃;

DOI:10.1021/jo0609531

upstream raw materials:

1,2-O-isopropylidene-5-O-p-toluenesulfonyl-α-D-erythro-ketofuranos-3-ulose

sodium cyanide

1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose

Downstream raw materials:

3-C-cyano-1,2-O-isopropylidene-3-O-mesyl-5-O-tosyl-α-D-ribofuranose

1,2-O-isopropylidene-3-spiro-5'-(4'-amino-1',2'-oxathiole-2',2'-dioxide)-5-O-tosyl-α-D-ribofuranose

(1R,2R,6R,8R,12S,14S)-12-benzyloxycarbonylmethyl-10,13-diaza-4,4-dimethyl-16,16-dioxide-11-oxo-3,5,7,17-tetraoxa-16-thio-pentacyclo[9.6.0.0^2,6.0^1,14.0^10,14]heptadecane

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