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

Base Information

• Chemical Name: phenyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-1-thio-α-D-mannopyranoside
• CAS No.: 173725-87-6
• Molecular Formula: C₃₇H₃₈O₈S
• Molecular Weight: 642.77

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

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

Chemical Property:

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

There total 1 articles about phenyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-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: 97.0%

succinic acid anhydride (108-30-5) + phenyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (127299-77-8) → phenyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-1-thio-α-D-mannopyranoside (173725-87-6)

Guidance literature:

With dmap; In pyridine; at 25 ℃; for 24h;

DOI:10.1016/0040-4039(95)01952-E

Reference yield: 57.0%

phenyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-1-thio-α-D-mannopyranoside (173725-87-6) + benzyl 2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside → benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[1,4-dioxo-4-(phenyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranosid-2-O-yl)butyl]-α-D-glucopyranoside (316188-08-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1002/1522-2675(20001004)83:10<2655::AID-HLCA2655>3.0.CO;2-U

Reference yield: 52.0%

benzyl 2-O-benzoyl-6-O-benzyl-3-O-chloroacetyl-α-D-glucopyranoside (173725-89-8) + phenyl 3,4,6-tri-O-benzyl-2-(3-hydroxycarbonyl)propionyl-1-thio-α-D-mannopyranoside (173725-87-6) → Succinic acid (2R,3R,4S,5R,6S)-5-benzoyloxy-6-benzyloxy-2-benzyloxymethyl-4-(2-chloro-acetoxy)-tetrahydro-pyran-3-yl ester (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester (173725-90-1)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃; for 5h;

DOI:10.1016/0040-4039(95)01952-E

upstream raw materials:

succinic acid anhydride

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

Downstream raw materials:

Succinic acid (2R,3R,4S,5R,6S)-5-benzoyloxy-6-benzyloxy-2-benzyloxymethyl-4-(2-chloro-acetoxy)-tetrahydro-pyran-3-yl ester (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[1,4-dioxo-4-(phenyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranosid-2-O-yl)butyl]-α-D-glucopyranoside

benzyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1-> 4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside 2',3-succinate

benzyl 2-O-benzoyl-6-O-benzyl-3-O-[1,4-dioxo-4-(phenyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranosid-2-O-yl)butyl]-α-D-glucopyranoside

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