methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Base Information

Chemical Name:methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
CAS No.:475672-29-8
Molecular Formula:C₂₇H₃₉NO₁₁
Molecular Weight:553.607
Hs Code.:

Synonyms:methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

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Chemical Property of methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

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Technology Process of methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

There total 3 articles about methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 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: 100.0%

: 1445-45-0
Trimethyl orthoacetate

: 475672-28-7
methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

: 475672-29-8
methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Guidance literature:: Trimethyl orthoacetate; methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside; With toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 1h;

With water; acetic acid; at 20 ℃; for 0.5h; Further stages.;
DOI:10.1002/1099-0690(200208)2002:15<2486::AID-EJOC2486>3.0.CO;2-E

Reference yield:

: Acetic acid (3R,4R,5S,6S)-4-acetoxy-5-benzyloxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester

: 475672-29-8
methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 84 percent / TMSOTf / CH₂Cl₂ / 7 h / -78 - 5 °C

2.1: 98 percent / NaOMe / methanol; CH₂Cl₂

3.1: p-toluenesulfonic acid / acetonitrile / 1 h / 20 °C

3.2: 100 percent / AcOH; water / 0.5 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane; acetonitrile;
DOI:10.1002/1099-0690(200208)2002:15<2486::AID-EJOC2486>3.0.CO;2-E

Reference yield:

: 475672-27-6
methyl (2,3-di-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

: 475672-29-8
methyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / NaOMe / methanol; CH₂Cl₂

2.1: p-toluenesulfonic acid / acetonitrile / 1 h / 20 °C

2.2: 100 percent / AcOH; water / 0.5 h / 20 °C

With sodium methylate; toluene-4-sulfonic acid; In methanol; dichloromethane; acetonitrile;
DOI:10.1002/1099-0690(200208)2002:15<2486::AID-EJOC2486>3.0.CO;2-E