.alpha.-D-Glucofuranuronic acid, 1,2-O-(1-methylethylidene)-, .gamma.-lactone, 4-methylbenzenesulfonate

Base Information

• Chemical Name: .alpha.-D-Glucofuranuronic acid, 1,2-O-(1-methylethylidene)-, .gamma.-lactone, 4-methylbenzenesulfonate
• CAS No.: 55263-78-0
• Molecular Formula: C16H18O8S
• Molecular Weight: 370.37

Synonyms:.alpha.-D-Glucofuranuronic acid, 1,2-O-(1-methylethylidene)-, .gamma.-lactone, 4-methylbenzenesulfonate

Chemical Property of .alpha.-D-Glucofuranuronic acid, 1,2-O-(1-methylethylidene)-, .gamma.-lactone, 4-methylbenzenesulfonate

Chemical Property:

• Melting Point: 185 - 187 °C
• PSA: 105.74000
• LogP: 1.95150

Purity/Quality:

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Technology Process of .alpha.-D-Glucofuranuronic acid, 1,2-O-(1-methylethylidene)-, .gamma.-lactone, 4-methylbenzenesulfonate

There total 5 articles about .alpha.-D-Glucofuranuronic acid, 1,2-O-(1-methylethylidene)-, .gamma.-lactone, 4-methylbenzenesulfonate 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%

toluene-4-sulfonic acid (104-15-4) + D-glucurono-3,6-lactone acetonide (3067-56-9,20513-98-8,25159-39-1,26623-22-3,29514-28-1,85080-95-1) → 1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-α-D-glucofuranurono-6,3-lactone (55263-78-0)

Guidance literature:

DOI:10.1016/S0040-4039(01)92419-0

Reference yield: 88.0%

p-toluenesulfonyl chloride (98-59-9) + 1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone (20513-98-8) → 1,2-O-isopropylidene-5-O-tosyl-α-D-glucuronolactone (55263-78-0)

Guidance literature:

With pyridine;

DOI:10.1246/cl.1987.123

Reference yield: 75.0%

p-toluenesulfonyl chloride (98-59-9) + D-glucurono-3,6-lactone acetonide (3067-56-9,20513-98-8,25159-39-1,26623-22-3,29514-28-1,85080-95-1) → 1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-α-D-glucofuranurono-6,3-lactone (55263-78-0)

Guidance literature:

With pyridine; In acetone; Ambient temperature;

DOI:10.1016/0008-6215(83)88356-6

upstream raw materials:

p-toluenesulfonyl chloride

D-glucurono-3,6-lactone acetonide

toluene-4-sulfonic acid

D-glucurono-6,3-lactone

Downstream raw materials:

5-azido-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-glucofuranose

1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-α-D-gluco-hexodialdo-1,4:6,3-difuranose

2,3,4-tri-O-acetyl-1,6-anhydro-β-L-idopyranose

3,6-di-O-acetyl-1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-α-D-glucofuranose

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