methyl O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-4-O-methyl-α-D-galactopyranosyl)-(1->4)-O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranoside

Base Information

• Chemical Name: methyl O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-4-O-methyl-α-D-galactopyranosyl)-(1->4)-O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranoside
• CAS No.: 258286-39-4
• Molecular Formula: C₆₅H₇₅N₉O₁₆
• Molecular Weight: 1238.36

Synonyms:methyl O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-4-O-methyl-α-D-galactopyranosyl)-(1->4)-O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranoside

Chemical Property of methyl O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-4-O-methyl-α-D-galactopyranosyl)-(1->4)-O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranoside

Chemical Property:

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Technology Process of methyl O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-4-O-methyl-α-D-galactopyranosyl)-(1->4)-O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranoside

There total 12 articles about methyl O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-4-O-methyl-α-D-galactopyranosyl)-(1->4)-O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranoside 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%

methyl O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranoside (258286-38-3) + methyl iodide (74-88-4) → methyl O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-4-O-methyl-α-D-galactopyranosyl)-(1->4)-O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranoside (258286-39-4)

Guidance literature:

methyl O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;

methyl iodide; In N,N-dimethyl-formamide; for 0.5h;

DOI:10.1016/s0040-4020(99)00869-8

Reference yield:

2-azido-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranosyl nitrate (128716-55-2) → methyl O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-4-O-methyl-α-D-galactopyranosyl)-(1->4)-O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranoside (258286-39-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 88 percent / ethanol / 3 h / 20 °C

2.1: 53 percent / de triflate de dimethyl (methylthio) sulfonium / CH₂Cl₂ / 3 h / 20 °C

3.1: 86 percent / AcOH 80 percent / 0.17 h / 80 °C

4.1: nBu₂SnO / acetonitrile / 14 h / 80 °C

4.2: 91 percent / NBu₄I / acetonitrile / 48 h / 20 °C

5.1: 51 percent / de triflate de dimethyl (methylthio) sulfonium / CH₂Cl₂ / 3 h / 20 °C

6.1: 90 percent / de l'acide acetique 80 percent / 0.17 h / 80 °C

7.1: nBu₂SnO / acetonitrile / 14 h / 80 °C

7.2: 90 percent / NBu₄I / acetonitrile / 48 h / 20 °C

8.1: NaH / dimethylformamide / 0.25 h / 0 °C

8.2: 81 percent / dimethylformamide / 0.5 h

With de l'acide acetique; de triflate de dimethyl (methylthio) sulfonium; sodium hydride; di(n-butyl)tin oxide; acetic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Substitution / 2.1: Substitution / 3.1: Hydrolysis / 4.1: Substitution / 4.2: Substitution / 5.1: Substitution / 6.1: Hydrolysis / 7.1: Substitution / 7.2: Substitution / 8.1: deprotonation / 8.2: Methylation;

DOI:10.1016/s0040-4020(99)00869-8

Reference yield:

O-ethyl S-(2-azido-6-O-benzyl-2-desoxy-3,4-O-isopropylidene-β-D-galactopyranosyl)xanthate (131326-60-8) → methyl O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-4-O-methyl-α-D-galactopyranosyl)-(1->4)-O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranoside (258286-39-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 53 percent / de triflate de dimethyl (methylthio) sulfonium / CH₂Cl₂ / 3 h / 20 °C

2.1: 86 percent / AcOH 80 percent / 0.17 h / 80 °C

3.1: nBu₂SnO / acetonitrile / 14 h / 80 °C

3.2: 91 percent / NBu₄I / acetonitrile / 48 h / 20 °C

4.1: 51 percent / de triflate de dimethyl (methylthio) sulfonium / CH₂Cl₂ / 3 h / 20 °C

5.1: 90 percent / de l'acide acetique 80 percent / 0.17 h / 80 °C

6.1: nBu₂SnO / acetonitrile / 14 h / 80 °C

6.2: 90 percent / NBu₄I / acetonitrile / 48 h / 20 °C

7.1: NaH / dimethylformamide / 0.25 h / 0 °C

7.2: 81 percent / dimethylformamide / 0.5 h

With de l'acide acetique; de triflate de dimethyl (methylthio) sulfonium; sodium hydride; di(n-butyl)tin oxide; acetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Substitution / 2.1: Hydrolysis / 3.1: Substitution / 3.2: Substitution / 4.1: Substitution / 5.1: Hydrolysis / 6.1: Substitution / 6.2: Substitution / 7.1: deprotonation / 7.2: Methylation;

DOI:10.1016/s0040-4020(99)00869-8

upstream raw materials:

methyl O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-O-(2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-desoxy-3-O-p-methoxybenzyl-α-D-galactopyranoside

methyl iodide

2-azido-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-β-D-galactopyranosyl nitrate

2-azido-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranosyl nitrate

Downstream raw materials:

methyl O-(2-azido-6-O-benzyl-2-desoxy-4-O-methyl-α-D-galactopyranosyl)-(1->4)-O-(2-azido-6-O-benzyl-2-desoxy-α-D-galactopyranosyl)-(1->4)-2-azido-6-O-benzyl-2-desoxy-α-D-galactopyranoside

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