Methyl 2,4-di-O-benzyl-3-O-(4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Base Information

• Chemical Name: Methyl 2,4-di-O-benzyl-3-O-(4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside
• CAS No.: 144174-63-0
• Molecular Formula: C₃₇H₄₆O₉
• Molecular Weight: 634.767

Synonyms:Methyl 2,4-di-O-benzyl-3-O-(4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Chemical Property of Methyl 2,4-di-O-benzyl-3-O-(4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of Methyl 2,4-di-O-benzyl-3-O-(4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

There total 7 articles about Methyl 2,4-di-O-benzyl-3-O-(4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 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: 78.0%

benzyl bromide (100-39-0) + methyl 2,4-di-O-benzyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside (92975-97-8) → Methyl 2,4-di-O-benzyl-3-O-(4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside (144174-63-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; paraffin; for 18h;

DOI:10.1016/0008-6215(93)84227-W

Reference yield:

methyl 3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside (69558-09-4) → Methyl 2,4-di-O-benzyl-3-O-(4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside (144174-63-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) sodium hydride

2: 1) 1,4-diazabicyclo<2.2.2>octane, 2) mercuric chloride, mercuric oxide / 1) tris(triphenylphosphine)-rhodium(I) chloride / 1) ethanol, benzene, water, reflux, 2) acetone, water

3: 65 percent / mercuric cyanide, molecular sieves (4 Angstroem) / acetonitrile / 3 h / Ambient temperature

4: 94 percent / sodium / methanol / 2 h

5: 85 percent / p-toluenesulphonic acid / CH₂Cl₂ / 3 h

6: 1) sodium hydride / 1) THF, oil, 2 h, 2) 18 h

With 1,4-diaza-bicyclo[2.2.2]octane; 4 A molecular sieve; sodium; mercury(II) cyanide; sodium hydride; toluene-4-sulfonic acid; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)80018-1

Reference yield:

benzyl bromide (100-39-0) → Methyl 2,4-di-O-benzyl-3-O-(4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside (144174-63-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) sodium hydride

2: 1) 1,4-diazabicyclo<2.2.2>octane, 2) mercuric chloride, mercuric oxide / 1) tris(triphenylphosphine)-rhodium(I) chloride / 1) ethanol, benzene, water, reflux, 2) acetone, water

3: 65 percent / mercuric cyanide, molecular sieves (4 Angstroem) / acetonitrile / 3 h / Ambient temperature

4: 94 percent / sodium / methanol / 2 h

5: 85 percent / p-toluenesulphonic acid / CH₂Cl₂ / 3 h

6: 1) sodium hydride / 1) THF, oil, 2 h, 2) 18 h

With 1,4-diaza-bicyclo[2.2.2]octane; 4 A molecular sieve; sodium; mercury(II) cyanide; sodium hydride; toluene-4-sulfonic acid; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)80018-1

upstream raw materials:

benzyl bromide

methyl 2,4-di-O-benzyl-3-O-(2,3-O-isopropylidene-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

methyl 2,4-di-O-benzyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Methyl 2,4-di-O-benzyl-3-O-α-L-rhamnopyranosyl-α-L-rhamnopyranoside

Downstream raw materials:

methyl (4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-2-[(2S,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-4-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester

Methyl 2,4-di-O-benzyl-3-O-<2,4-di-O-benzyl-3-O-(2-O-methyl-α-L-fucopyranosyl)-α-L-rhamnopyranosyl>-α-L-rhamnopyranoside

methyl O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

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