Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 864862-22-6
• Molecular Formula: C₁₉H₂₁N₃O₆S₂
• Molecular Weight: 451.524

Synonyms:Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

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Technology Process of Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

There total 2 articles about Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-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:

phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside (371123-22-7) → Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (864862-22-6)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethylaminopyridine; trifluoromethane sulfonic azide / methanol; CH₂Cl₂ / 16 h

2: 3.58 g / pyridine / 8 h

With pyridine; dmap; triflic azide; In methanol; dichloromethane;

DOI:10.1039/b505865a

Reference yield:

p-toluenesulfonyl chloride (98-59-9) + phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside (166516-67-2) → Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (864862-22-6)

Guidance literature:

With pyridine; for 8h;

DOI:10.1039/b505865a

Reference yield: 89.0%

Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (864862-22-6) → phenyl 2,6-diazido-2,6-dideoxy-1-thio-β-D-glucopyranoside (663938-12-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; for 18h; Heating;

DOI:10.1039/b505865a

upstream raw materials:

p-toluenesulfonyl chloride

phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside

phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside

Downstream raw materials:

phenyl 2,6-diazido-2,6-dideoxy-1-thio-β-D-glucopyranoside

(1R,3R,4R,6R)-1-O-(2',6'-azido-2',6'-deoxy-3',4'-di-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexane-1,3-diol

(1S,3S,4S,6S)-1-O-(2',6'-azido-2',6'-deoxy-3',4'-di-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexane-1,3-diol

(2S,3R,4R,5R,6R)-3-Azido-6-azidomethyl-4,5-bis-benzyloxy-2-phenylsulfanyl-tetrahydro-pyran

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