methyl 4,6-O-isopropylidene-5-thio-3-O-toluene-p-sulphonyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 4,6-O-isopropylidene-5-thio-3-O-toluene-p-sulphonyl-α-D-glucopyranoside
• CAS No.: 72045-07-9
• Molecular Formula: C₁₇H₂₄O₇S₂
• Molecular Weight: 404.505

Synonyms:methyl 4,6-O-isopropylidene-5-thio-3-O-toluene-p-sulphonyl-α-D-glucopyranoside

Chemical Property of methyl 4,6-O-isopropylidene-5-thio-3-O-toluene-p-sulphonyl-α-D-glucopyranoside

Chemical Property:

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Technology Process of methyl 4,6-O-isopropylidene-5-thio-3-O-toluene-p-sulphonyl-α-D-glucopyranoside

There total 2 articles about methyl 4,6-O-isopropylidene-5-thio-3-O-toluene-p-sulphonyl-α-D-glucopyranoside 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:

6-O-acetyl-5-S-acetyl-1,2-O-isopropylidene-5-thio-3-toluene-p-sulphonyl-α-D-glucofuranose (50680-04-1) → methyl 4,6-O-isopropylidene-5-thio-3-O-toluene-p-sulphonyl-α-D-glucopyranoside (72045-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 4.8 g / conc hydrochloric acid / 6 h / Heating

2: 4.9 g / toluene-p-sulphonic acid / acetone

With hydrogenchloride; toluene-4-sulfonic acid; In acetone;

DOI:10.1016/0008-6215(86)80034-9

Reference yield:

methyl 5-thio-3-o-toluene-p-sulphonyl-α-D-glucopyranoside (72045-06-8) + 2,2-dimethoxy-propane (77-76-9) → methyl 4,6-O-isopropylidene-5-thio-3-O-toluene-p-sulphonyl-α-D-glucopyranoside (72045-07-9)

Guidance literature:

With toluene-4-sulfonic acid; In acetone;

DOI:10.1016/0008-6215(86)80034-9

Reference yield: 57.0%

methanesulfonyl chloride (124-63-0) + methyl 4,6-O-isopropylidene-5-thio-3-O-toluene-p-sulphonyl-α-D-glucopyranoside (72045-07-9) → methyl 4,6-O-isopropylidene-2-O-methylsulphonyl-5-thio-3-O-p-tolylsulphonyl-α-D-glucopyranoside (114768-52-4)

Guidance literature:

With triethylamine; In dichloromethane; at -10 ℃; for 0.166667h;

upstream raw materials:

methyl 5-thio-3-o-toluene-p-sulphonyl-α-D-glucopyranoside

2,2-dimethoxy-propane

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

Downstream raw materials:

methyl 4,6-O-isopropylidene-2-O-methylsulphonyl-5-thio-3-O-p-tolylsulphonyl-α-D-glucopyranoside

5-thio-D-altrose

5-hydroxymethyltiophene-2-carbaldehyde

Toluene-4-sulfonic acid (2S,3S,4S,5R)-2-dimethoxymethyl-4-hydroxy-5-hydroxymethyl-tetrahydro-thiophen-3-yl ester

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