methyl 3-acetyl-2,3-dideoxy-2-(2,4-dimethoxybenzylamino)-5,6-O-isopropylidene-α-D-mannofuranoside

Base Information

Chemical Name:methyl 3-acetyl-2,3-dideoxy-2-(2,4-dimethoxybenzylamino)-5,6-O-isopropylidene-α-D-mannofuranoside
CAS No.:114827-92-8
Molecular Formula:C₂₁H₃₁NO₇
Molecular Weight:409.48
Hs Code.:

Synonyms:methyl 3-acetyl-2,3-dideoxy-2-(2,4-dimethoxybenzylamino)-5,6-O-isopropylidene-α-D-mannofuranoside

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Chemical Property of methyl 3-acetyl-2,3-dideoxy-2-(2,4-dimethoxybenzylamino)-5,6-O-isopropylidene-α-D-mannofuranoside

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Technology Process of methyl 3-acetyl-2,3-dideoxy-2-(2,4-dimethoxybenzylamino)-5,6-O-isopropylidene-α-D-mannofuranoside

There total 17 articles about methyl 3-acetyl-2,3-dideoxy-2-(2,4-dimethoxybenzylamino)-5,6-O-isopropylidene-α-D-mannofuranoside 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: 76.0%

: 917-54-4
methyllithium

: 114827-88-2
(1R,2S,4S,5S)-6-(2,4-dimethoxybenzyl)-2-<(1R)-1,2-isopropylidenedioxyethyl>-4-methoxy-3-oxa-6-azabicyclo<3.2.0>heptan-7-one

: 114827-92-8
methyl 3-acetyl-2,3-dideoxy-2-(2,4-dimethoxybenzylamino)-5,6-O-isopropylidene-α-D-mannofuranoside

Guidance literature:: In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.25h;
DOI:10.1246/bcsj.62.3950

Reference yield:

: (1R,3S,4S,5R,8R)-4-(2,4-dimethoxybenzylamino)-8-hydroxymethyl-3-methoxy-2,7-dioxabicyclo<3.3.0>octan-6-one

: 114827-92-8
methyl 3-acetyl-2,3-dideoxy-2-(2,4-dimethoxybenzylamino)-5,6-O-isopropylidene-α-D-mannofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 67 percent / MeMgBr / tetrahydrofuran / 0.5 h

2: 92 percent / pyridinium p-toluenesulfonate / dimethylformamide / 18 h / Ambient temperature

3: 76 percent / diethyl ether; tetrahydrofuran / 0.25 h / -78 °C

With methylmagnesium bromide; pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.62.3950

Reference yield:

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 114827-92-8
methyl 3-acetyl-2,3-dideoxy-2-(2,4-dimethoxybenzylamino)-5,6-O-isopropylidene-α-D-mannofuranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) 55percent NaH (in mineral oil), 2.) acetic acid / 1.) DMSO, 1.5 h, room temperature, 2.) DMSO, 20 h, room temperature

2: 45 percent / DCC / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 52 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Heating

4: 98 percent / silicagel powder, NaBH₄ / methanol / 0.25 h

5: 79 percent / H₂O, 1,8-diazabicyclo<5.4.0>undec-7-ene / pyridine / 0.75 h / Heating

6: 86 percent / Ag₂O / dimethylformamide / 4 h / Ambient temperature

7: 76 percent / diethyl ether; tetrahydrofuran / 0.25 h / -78 °C

With sodium tetrahydroborate; water; silica gel; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; silver(l) oxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1246/bcsj.62.3950