p-methoxyphenyl 6-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-allopyranoside

Base Information

Chemical Name:p-methoxyphenyl 6-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-allopyranoside
CAS No.:197449-45-9
Molecular Formula:C₁₇H₂₀Cl₃NO₈
Molecular Weight:472.707
Hs Code.:

Synonyms:p-methoxyphenyl 6-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-allopyranoside

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Chemical Property of p-methoxyphenyl 6-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-allopyranoside

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Technology Process of p-methoxyphenyl 6-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-allopyranoside

There total 7 articles about p-methoxyphenyl 6-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-allopyranoside 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: 77.0%

: 197449-42-6
p-methoxyphenyl 6-O-acetyl-2,3,4-trideoxy-2-trichloroacetamido-α-D-erythro-hex-3-enopyranoside

: 197449-45-9
p-methoxyphenyl 6-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-allopyranoside

: p-methoxyphenyl 6-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-galactopyranoside

Guidance literature:: With ruthenium trichloride; sodium periodate; In water; ethyl acetate; acetonitrile; at -11 ℃; for 0.0666667h;
DOI:10.1246/bcsj.70.2535

Reference yield:

: 76223-29-5,76223-30-8,143134-83-2,76223-28-4
4'-methoxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-1-O-α-D-erythro-hex-2-enopyranoside

: 197449-45-9
p-methoxyphenyl 6-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-allopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / triethylamine / methanol / 7 h / 70 °C

2: 99 percent / Pseudomonas lipase PS / 48 h / 20 °C

3: 100 percent / 1,8-diazabicyclo[5.4.0]-7-undecene / CH₂Cl₂ / 0.25 h / -17 °C

4: 54 percent / molecular sieves 4A / diphenyl ether / 0.58 h / 210 °C

5: 77 percent / ruthenium(III) chloride trihydrate; sodium metaperiodate / acetonitrile; ethyl acetate; H₂O / 0.07 h / -11 °C

With ruthenium trichloride; sodium periodate; 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; Pseudomonas lipase PS; In methanol; diphenylether; dichloromethane; water; ethyl acetate; acetonitrile; 1: Deacetylation / 2: Acetylation / 3: Addition / 4: Rearrangement / 5: Oxidation;
DOI:10.1246/bcsj.70.2535

Reference yield:

: 150-76-5
4-methoxy-phenol

: 197449-45-9
p-methoxyphenyl 6-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-allopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / BF₃*OEt₂ / toluene

2: 100 percent / triethylamine / methanol / 7 h / 70 °C

3: 99 percent / Pseudomonas lipase PS / 48 h / 20 °C

4: 100 percent / 1,8-diazabicyclo[5.4.0]-7-undecene / CH₂Cl₂ / 0.25 h / -17 °C

5: 54 percent / molecular sieves 4A / diphenyl ether / 0.58 h / 210 °C

6: 77 percent / ruthenium(III) chloride trihydrate; sodium metaperiodate / acetonitrile; ethyl acetate; H₂O / 0.07 h / -11 °C

With ruthenium trichloride; sodium periodate; 4 A molecular sieve; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; Pseudomonas lipase PS; In methanol; diphenylether; dichloromethane; water; ethyl acetate; toluene; acetonitrile; 1: glycosylation; Ferrier rearrangement / 2: Deacetylation / 3: Acetylation / 4: Addition / 5: Rearrangement / 6: Oxidation;
DOI:10.1246/bcsj.70.2535