Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester
• CAS No.: 142866-02-2
• Molecular Formula: C₁₅H₁₈O₇S
• Molecular Weight: 342.37

Synonyms:Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester

There total 1 articles about Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-3-yl 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: 75.0%

4-O-Acetyl-3-O-tert-butyldimethylsilyl-6-O-tosyl-D-glucal (129693-97-6) → Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester (142866-02-2)

Guidance literature:

With triethylamine hydrofluoride; In acetonitrile; at 23 ℃;

DOI:10.1021/jo00044a010

Reference yield: 91.0%

Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester (142866-02-2) + 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-1-trichloroacetimido-α-D-glucopyranose (142865-94-9) → 4-O-acetyl-3-O-(4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-α,β-D-glucopyranosyl)-2-deoxy-6-O-p-toluenesulfonyl-D-arabino-hex-1-enitol (142866-03-3,142926-93-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -78 ℃; for 0.0833333h;

DOI:10.1021/jo00044a010

Reference yield: 89.0%

Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester (142866-02-2) + 6-bromo-3,4-bis-O-(tert-butyldimethylsilyl)-2,6-dideoxy-2-iodo-β-D-glucopyranosyl fluoride (493033-92-4) → 3-O-[2-deoxy-2-iodo-3,4-bis-O-(tert-butyldimethyl)silyl-6-bromo-β-D-glucopyranosyl]-2-deoxy-4-O-acetyl-6-O-p-toluenesulfonyl-D-arabino-hex-1-enitol

Guidance literature:

With silver perchlorate; tin(ll) chloride; In diethyl ether; at -10 ℃; for 0.166667h;

DOI:10.1021/ja048493l

upstream raw materials:

4-O-Acetyl-3-O-tert-butyldimethylsilyl-6-O-tosyl-D-glucal

Downstream raw materials:

4-O-acetyl-3-O-(4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-α,β-D-glucopyranosyl)-2-deoxy-6-O-p-toluenesulfonyl-D-arabino-hex-1-enitol

C₄₇H₅₇IO₁₈S₃

Acetic acid (2R,3S,4S,5R,6S)-6-[(2R,3S,4R)-3-acetoxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-4-yloxy]-4-hydroxy-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3S,4S,5R,6R)-6-[(2R,3S,4R)-3-acetoxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-4-yloxy]-4-hydroxy-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

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