methyl 4-O-benzoyl-6-deoxy-2,3-di-O-methyl-α-D-arabino-hex-5-enopyranoside

Base Information

• Chemical Name: methyl 4-O-benzoyl-6-deoxy-2,3-di-O-methyl-α-D-arabino-hex-5-enopyranoside
• CAS No.: 95640-26-9
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.331

Synonyms:methyl 4-O-benzoyl-6-deoxy-2,3-di-O-methyl-α-D-arabino-hex-5-enopyranoside

Chemical Property of methyl 4-O-benzoyl-6-deoxy-2,3-di-O-methyl-α-D-arabino-hex-5-enopyranoside

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Technology Process of methyl 4-O-benzoyl-6-deoxy-2,3-di-O-methyl-α-D-arabino-hex-5-enopyranoside

There total 4 articles about methyl 4-O-benzoyl-6-deoxy-2,3-di-O-methyl-α-D-arabino-hex-5-enopyranoside 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: 87.0%

methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-α-D-altropyranoside (82159-74-8) → methyl 4-O-benzoyl-6-deoxy-2,3-di-O-methyl-α-D-arabino-hex-5-enopyranoside (95640-26-9)

Guidance literature:

With silver fluoride; In pyridine; Ambient temperature;

DOI:10.1016/S0008-6215(00)90774-2

Reference yield: 67.0%

methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside (56543-17-0) → methyl 4-O-benzoyl-6-deoxy-2,3-di-O-methyl-α-D-xylo-hex-5-enopyranoside (95640-26-9,95640-29-2,120104-33-8)

Guidance literature:

With C₈K; In tetrahydrofuran; at -10 ℃; for 0.25h;

DOI:10.1021/jo00271a012

Reference yield: 32.0%

methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside (56543-17-0) → methyl 6-O-benzoyl-2,3-di-O-methyl-α-D-glucopyranoside (51517-51-2) + methyl 4,6-di-O-benzoyl-2,3-di-O-methyl-α-D-glucopyranoside (62847-87-4) + methyl 4-O-benzoyl-6-deoxy-2,3-di-O-methyl-α-D-xylo-hex-5-enopyranoside (95640-26-9,95640-29-2,120104-33-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 110 ℃; for 3.5h;

DOI:10.1246/bcsj.66.1156

upstream raw materials:

methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside

methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-α-D-altropyranoside

methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-altropyranoside

Downstream raw materials:

2L-2,3/4-2-benzoyloxy-3,4-dimethoxycyclohex-5-enone

2L-2,3/4,5-2-benzoyloxy-5-hydroxy-3,4-dimethoxycyclohexanone

1,6-anhydro-2,3-di-O-methyl-4-O-benzoyl-5-C-hydroxy-β-L-idopyranose

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