methyl (2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl (2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 144431-90-3
• Molecular Formula: C₇₅H₇₆O₁₇
• Molecular Weight: 1249.42
• Mol file: 144431-90-3.mol

Synonyms:methyl (2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

Chemical Property of methyl (2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

There total 13 articles about methyl (2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-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: 92.0%

methyl [2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside (90164-77-5) + 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate (161007-95-0) → methyl (2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside (144431-90-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃; for 15h;

DOI:10.1080/07328309908544033

Reference yield:

methyl 4-O-benzyl-α-L-rhamnopyranoside (25019-69-6) → methyl (2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside (144431-90-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Bu₂SnO / toluene

1.2: Bu₄NI / dioxane

2.1: 76 percent / sym-collidine; AgOTf / CH₂Cl₂ / 5 h / 20 °C

3.1: H₂ / 1,5-COD-bis(trimethylphosphine)iridium hexafluorophosphate / tetrahydrofuran / 3 h

4.1: HgO; HgCl₂ / acetone; H₂O / 5 h / 20 °C

5.1: TMSCl; pyridine / CH₂Cl₂ / 3 h / 20 °C

5.2: triflic anhydride / diethyl ether / 40 h / 4 °C

With pyridine; 2,4,6-trimethyl-pyridine; chloro-trimethyl-silane; hydrogen; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; mercury dichloride; mercury(II) oxide; 1,5-COD-bis(trimethylphosphine)iridium hexafluorophosphate; In tetrahydrofuran; dichloromethane; water; acetone; toluene; 1.1: Metallation / 1.2: Substitution / 2.1: Substitution / 3.1: Isomerization / 4.1: Hydrolysis / 5.1: Substitution / 5.2: Substitution;

DOI:10.1080/07328309908544033

Reference yield:

methyl 3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside (69558-09-4) → methyl (2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside (144431-90-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 76 percent / sym-collidine; AgOTf / CH₂Cl₂ / 5 h / 20 °C

2.1: H₂ / 1,5-COD-bis(trimethylphosphine)iridium hexafluorophosphate / tetrahydrofuran / 3 h

3.1: HgO; HgCl₂ / acetone; H₂O / 5 h / 20 °C

4.1: TMSCl; pyridine / CH₂Cl₂ / 3 h / 20 °C

4.2: triflic anhydride / diethyl ether / 40 h / 4 °C

With pyridine; 2,4,6-trimethyl-pyridine; chloro-trimethyl-silane; hydrogen; silver trifluoromethanesulfonate; mercury dichloride; mercury(II) oxide; 1,5-COD-bis(trimethylphosphine)iridium hexafluorophosphate; In tetrahydrofuran; dichloromethane; water; acetone; 1.1: Substitution / 2.1: Isomerization / 3.1: Hydrolysis / 4.1: Substitution / 4.2: Substitution;

DOI:10.1080/07328309908544033

upstream raw materials:

methyl [2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside

2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide

2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride

Downstream raw materials:

methyl (2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-[α-D-glucopyranosyl-(1->3)]-α-L-rhamnopyranoside