phenyl 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
• CAS No.: 340161-04-8
• Molecular Formula: C₆₂H₆₄O₁₁S
• Molecular Weight: 1017.25

Synonyms:phenyl 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Chemical Property:

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Technology Process of phenyl 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

There total 4 articles about phenyl 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 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%

1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside (68567-54-4) + phenyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (127299-77-8) → phenyl 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (340161-04-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 0.166667h; stereoselective reaction; Sonication;

DOI:10.1021/jo8019835

Reference yield: 72.0%

O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-manno-pyranose) trichloroacetimidate → phenyl 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (340161-04-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; sodium hydrogencarbonate; In dichloromethane;

Reference yield: 72.0%

2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate (108869-64-3,130177-78-5,129163-12-8) + phenyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (127299-77-8) → phenyl 2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (340161-04-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -10 ℃; for 0.5h;

DOI:10.1128/AAC.46.12.3869-3876.2002

upstream raw materials:

2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate

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

1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Downstream raw materials:

Acetic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

Phenyl 2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

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