(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2H-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2H-pyran-3-ol
• CAS No.: 1070321-07-1
• Molecular Formula: C₂₆H₂₈O₅S
• Molecular Weight: 452.571

Synonyms:(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2H-pyran-3-ol

Chemical Property of (2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2H-pyran-3-ol

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Technology Process of (2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2H-pyran-3-ol

There total 1 articles about (2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2H-pyran-3-ol 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: 97.0%

phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (158716-07-5) → (2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2H-pyran-3-ol (1070321-07-1)

Guidance literature:

phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside; With borane-THF; In toluene; for 0.25h; Inert atmosphere; Cooling with ice;

With di-n-butylboryl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/ja8028137

Reference yield: 90.0%

(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2H-pyran-3-ol (1070321-07-1) + n-hexadecanoyl chloride (112-67-4) → phenyl 3,4-di-O-benzyl-6-O-hexadecanoyl-1-thio-α-D-mannopyranoside (1336875-76-3)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; regioselective reaction;

DOI:10.1021/jm2008419

Reference yield: 84.0%

(2R,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2H-pyran-3-ol (1070321-07-1) + benzoyl chloride (98-88-4) → C40H36O7S

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 26h;

DOI:10.1021/ja8028137

upstream raw materials:

phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

phenyl 3,4-di-O-benzyl-6-O-hexadecanoyl-1-thio-α-D-mannopyranoside

phenyl 2-O-(2-azidomethylbenzoyl)-3,4-di-O-benzyl-6-O-hexadecanoyl-1-thio-α-D-mannopyranoside

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