methyl 4,6-O-cyclohexylidene-2,3-O-p-methoxybenzylidene-1-thio-α-D-manopyranoside

Base Information

• Chemical Name: methyl 4,6-O-cyclohexylidene-2,3-O-p-methoxybenzylidene-1-thio-α-D-manopyranoside
• CAS No.: 215721-96-3
• Molecular Formula: C₂₁H₂₈O₆S
• Molecular Weight: 408.516

Synonyms:methyl 4,6-O-cyclohexylidene-2,3-O-p-methoxybenzylidene-1-thio-α-D-manopyranoside

Chemical Property of methyl 4,6-O-cyclohexylidene-2,3-O-p-methoxybenzylidene-1-thio-α-D-manopyranoside

Chemical Property:

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Technology Process of methyl 4,6-O-cyclohexylidene-2,3-O-p-methoxybenzylidene-1-thio-α-D-manopyranoside

There total 4 articles about methyl 4,6-O-cyclohexylidene-2,3-O-p-methoxybenzylidene-1-thio-α-D-manopyranoside 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: 81.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + methyl 4,6-O-cyclohexylidene-1-thio-α-D-mannopyranoside (215721-95-2) → methyl 4,6-O-cyclohexylidene-2,3-O-p-methoxybenzylidene-1-thio-α-D-manopyranoside (215721-96-3)

Guidance literature:

With pyridinium p-toluenesulfonate; In acetonitrile; at 20 ℃; for 0.666667h;

DOI:10.1016/S0040-4020(01)00300-3

Reference yield:

methyl 1-thio-α-D-mannopyranoside (80734-76-5) → methyl 4,6-O-cyclohexylidene-2,3-O-p-methoxybenzylidene-1-thio-α-D-manopyranoside (215721-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / CSA; Drierite / acetonitrile; dimethylformamide / 1.5 h

2: 81 percent / PPTS / acetonitrile / 0.67 h / 20 °C

With calcium sulfate; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(01)00300-3

Reference yield:

cycloxexanone dimethyl ketal (933-40-4) → methyl 4,6-O-cyclohexylidene-2,3-O-p-methoxybenzylidene-1-thio-α-D-manopyranoside (215721-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / CSA; Drierite / acetonitrile; dimethylformamide / 1.5 h

2: 81 percent / PPTS / acetonitrile / 0.67 h / 20 °C

With calcium sulfate; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(01)00300-3

upstream raw materials:

p-Anisaldehyde dimethyl acetal

methyl 4,6-O-cyclohexylidene-1-thio-α-D-mannopyranoside

cycloxexanone dimethyl ketal

methyl 1-thio-α-D-mannopyranoside

Downstream raw materials:

methyl 4,6-O-cyclohexylidene-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

methyl 4,6-O-cyclohexylidene-2-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-1-thio-α-D-mannopyranoside

C₇₂H₇₉NO₁₄SSi

tert-Butyl-[(4aR,6R,7S,8S,8aR)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-6-methylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-diphenyl-silane

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