methyl 2,3-di-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside

Base Information

• Chemical Name: methyl 2,3-di-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside
• CAS No.: 920274-32-4
• Molecular Formula: C₅₁H₅₈O₁₁
• Molecular Weight: 847.015
• Mol file: 920274-32-4.mol

Synonyms:methyl 2,3-di-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside

Chemical Property of methyl 2,3-di-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3-di-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside

There total 6 articles about methyl 2,3-di-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside 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: 96.0%

methyl 2,3-di-O-acetyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside (920274-31-3) + benzyl bromide (100-39-0) → methyl 2,3-di-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside (920274-32-4)

Guidance literature:

methyl 2,3-di-O-acetyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside; With sodium methylate; In methanol; dichloromethane; for 12h; pH=10;

benzyl bromide; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1021/jo061821a

Reference yield:

(2S,3R,4R)-2-((R)-1,2-Dihydroxy-ethyl)-5-p-tolylsulfanyl-tetrahydro-furan-3,4-diol → methyl 2,3-di-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside (920274-32-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: p-TsOH / acetone / 4 h / 20 °C

1.2: pyridine / 6 h / 0 °C

2.1: 94 percent / molecular sieves 4 Angstroem; N-iodosuccinimide; silver triflate / CH₂Cl₂ / 0.33 h / 0 °C

3.1: NaOCH₃ / methanol; CH₂Cl₂ / 12 h / pH 10

3.2: 96 percent / NaH / dimethylformamide / 12 h / 20 °C

With N-iodo-succinimide; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; In methanol; dichloromethane; acetone;

DOI:10.1021/jo061821a

Reference yield:

Acetic acid (2S,3S,4R)-4-acetoxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-p-tolylsulfanyl-tetrahydro-furan-3-yl ester (920274-27-7) → methyl 2,3-di-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside (920274-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 94 percent / molecular sieves 4 Angstroem; N-iodosuccinimide; silver triflate / CH₂Cl₂ / 0.33 h / 0 °C

2.1: NaOCH₃ / methanol; CH₂Cl₂ / 12 h / pH 10

2.2: 96 percent / NaH / dimethylformamide / 12 h / 20 °C

With N-iodo-succinimide; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1021/jo061821a

upstream raw materials:

methyl 2,3-di-O-acetyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside

benzyl bromide

Acetic acid (2S,3S,4R)-4-acetoxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-p-tolylsulfanyl-tetrahydro-furan-3-yl ester

methyl 2,3,5-tri-O-benzyl-6-O-trityl-β-D-galactofuranoside

Downstream raw materials:

methyl 3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->5)-2,3,6-tri-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside

methyl 2,3-di-O-acetyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->5)-2,3,6-tri-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside

methyl 5,6-O-isopropylidene-β-D-galactofuranosyl-(1->5)-2,3,6-tri-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside

methyl 2,3,6-tri-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside