ethyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->2)-3-O-allyl-4,6-benzylidene-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: ethyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->2)-3-O-allyl-4,6-benzylidene-1-thio-α-D-mannopyranoside
• CAS No.: 821805-15-6
• Molecular Formula: C₃₁H₄₀O₁₄S
• Molecular Weight: 668.716

Synonyms:ethyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->2)-3-O-allyl-4,6-benzylidene-1-thio-α-D-mannopyranoside

Chemical Property of ethyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->2)-3-O-allyl-4,6-benzylidene-1-thio-α-D-mannopyranoside

Chemical Property:

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Technology Process of ethyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->2)-3-O-allyl-4,6-benzylidene-1-thio-α-D-mannopyranoside

There total 1 articles about ethyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->2)-3-O-allyl-4,6-benzylidene-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: 58.0%

methyl 2,3,4-tri-O-acetyl-α,β-D-glucopyranosyluronate trichloroacetimidate + ethyl 3-O-allyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (319922-00-4) → ethyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->2)-3-O-allyl-4,6-benzylidene-1-thio-α-D-mannopyranoside (821805-15-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 2h;

DOI:10.1081/CAR-200040114

Reference yield: 71.0%

ethyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->2)-3-O-allyl-4,6-benzylidene-1-thio-α-D-mannopyranoside (821805-15-6) → ethyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->2)-3-O-allyl-6-O-benzyl-1-thio-α-D-mannopyranoside (821805-19-0)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 20 ℃; for 1.5h;

DOI:10.1081/CAR-200040114

Reference yield:

ethyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->2)-3-O-allyl-4,6-benzylidene-1-thio-α-D-mannopyranoside (821805-15-6) → (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-((2R,4aR,6R,7S,8S,8aR)-8-allyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tetrahydro-pyran-2-carboxylic acid

Guidance literature:

With water; sodium methylate; In methanol; at 20 ℃; for 1h; pH=12;

DOI:10.1081/CAR-200040114

upstream raw materials:

ethyl 3-O-allyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

ethyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->2)-3-O-allyl-6-O-benzyl-1-thio-α-D-mannopyranoside

ethyl (benzyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->2)-3-O-allyl-4,6-benzylidene-1-thio-α-D-mannopyranoside

ethyl (benzyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->2)-3-O-allyl-4,6-di-O-benzyl-1-thio-α-D-mannopyranoside

ethyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->2)-[(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-(1->4)]-3-O-allyl-6-O-benzyl-1-thio-α-D-mannopyranoside

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