methyl 4-O-<2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl>-2,3-O-isopropylidene-α-L-rhamonopyranoside

Base Information

Chemical Name:methyl 4-O-<2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl>-2,3-O-isopropylidene-α-L-rhamonopyranoside
CAS No.:118281-89-3
Molecular Formula:C₂₆H₃₇NO₁₁
Molecular Weight:539.58
Hs Code.:

Synonyms:methyl 4-O-<2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl>-2,3-O-isopropylidene-α-L-rhamonopyranoside

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Chemical Property of methyl 4-O-<2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl>-2,3-O-isopropylidene-α-L-rhamonopyranoside

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Technology Process of methyl 4-O-<2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl>-2,3-O-isopropylidene-α-L-rhamonopyranoside

There total 6 articles about methyl 4-O-<2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl>-2,3-O-isopropylidene-α-L-rhamonopyranoside 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: 91.1%

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 118281-88-2
methyl 4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2,3-O-isopropylidene-α-L-rhamonopyranoside

: 118281-89-3
methyl 4-O-<2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl>-2,3-O-isopropylidene-α-L-rhamonopyranoside

Guidance literature:: With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 13h;
DOI:10.1016/0008-6215(88)84110-7

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 118281-89-3
methyl 4-O-<2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl>-2,3-O-isopropylidene-α-L-rhamonopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 54.7 percent / boron trifluoride etherate (BF₃*Et₂O) / CH₂Cl₂ / 4 h / 0 - 20 °C

2: 96 percent / bromine / CH₂Cl₂ / 0.25 h / 0 - 20 °C

3: 89.7 percent / molecular sieves (4A), nitrosyl terafluoroborate / CH₂Cl₂ / 1.75 h / 20 °C

4: 1.) MeOH, reflux, 3 h; 2.) MeOH, 0 deg C, 4 h

5: 91.1 percent / TsOH*H₂O / dimethylformamide / 13 h / 20 °C

With 4 A molecular sieve; bromine; nitrosonium tetrafluoroborate; toluene-4-sulfonic acid; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(88)84110-7

Reference yield:

: 79528-48-6
methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 118281-89-3
methyl 4-O-<2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl>-2,3-O-isopropylidene-α-L-rhamonopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / bromine / CH₂Cl₂ / 0.25 h / 0 - 20 °C

2: 89.7 percent / molecular sieves (4A), nitrosyl terafluoroborate / CH₂Cl₂ / 1.75 h / 20 °C

3: 1.) MeOH, reflux, 3 h; 2.) MeOH, 0 deg C, 4 h

4: 91.1 percent / TsOH*H₂O / dimethylformamide / 13 h / 20 °C

With 4 A molecular sieve; bromine; nitrosonium tetrafluoroborate; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(88)84110-7