6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole

Base Information

• Chemical Name: 6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole
• CAS No.: 218621-71-7
• Molecular Formula: C₁₅H₂₀O₇S
• Molecular Weight: 344.386
• Mol file: 218621-71-7.mol

Synonyms:6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole

Chemical Property of 6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole

There total 5 articles about 6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole 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: 90.0%

p-toluenesulfonyl chloride (98-59-9) + 1,2-O-isopropylidene-α-L-xylofuranose (114861-22-2) → 6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole (218621-71-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2005.02.140

Reference yield:

L-xylose (41546-31-0) → 6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole (218621-71-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) H₂SO₄, molecular sieves 13X; 2.) 0.25 M HCl / 1.) 35 deg C, 4 h; 2.) 1,2-dimethoxyethane, 50 deg C, 1 h

2: 61 percent / pyridine; CHCl₃ / 4 h / 20 °C

With hydrogenchloride; molecular sieve; sulfuric acid; In pyridine; chloroform;

DOI:10.1002/(SICI)1522-2675(19981111)81:11<2043::AID-HLCA2043>3.0.CO;2-6

Reference yield:

L-xylopyranose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) → 6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole (218621-71-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CuSO₄; H₂SO₄ / acetone / 36 h / 20 °C

1.2: 98 percent / aq. HCl / H₂O / 6 h

2.1: 71 percent / pyridine / CHCl₃ / 20 °C

With pyridine; sulfuric acid; copper(II) sulfate; In chloroform; acetone; 1.1: Condensation / 1.2: Hydrolysis / 2.1: Tosylation;

DOI:10.1080/15257770008033005

upstream raw materials:

p-toluenesulfonyl chloride

1,2-O-isopropylidene-α-L-xylofuranose

L-xylopyranose

L-xylose

Downstream raw materials:

L-idomethylonic acid

L-gulomethylonic acid

1,2-O-(1-methylethylidene)-3-deoxy-3-(hydroxymethyl)-5-O-benzyl-L-ribofuranose

1,2-O-(1-methylethylidene)-3-deoxy-3-methylene-5-O-benzyl-L-xylofuranose