methyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-β-L-galactopyranosyl]-β-L-glucopyranoside

Base Information

• Chemical Name: methyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-β-L-galactopyranosyl]-β-L-glucopyranoside
• CAS No.: 692740-49-1
• Molecular Formula: C₇₇H₈₅NO₁₅
• Molecular Weight: 1264.52
• Mol file: 692740-49-1.mol

Synonyms:

Chemical Property of methyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-β-L-galactopyranosyl]-β-L-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-β-L-galactopyranosyl]-β-L-glucopyranoside

There total 32 articles about methyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-β-L-galactopyranosyl]-β-L-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:

methyl 2-acetamido-4-O-(3,4,6-tri-O-benzyl-β-L-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-L-glucopyranoside (652972-20-8) + ethyl 2,3,4-tri-O-benzyl-1-thio-D-fucopyranoside (116391-11-8) → methyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-β-D-fucopyranosyl)-β-L-galactopyranosyl]-β-L-glucopyranoside + methyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-β-L-galactopyranosyl]-β-L-glucopyranoside (692740-49-1)

Guidance literature:

With di-tert-butyl-4-methylpyridine; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; at 0 - 20 ℃; for 14h;

DOI:10.1021/jo035789l

Reference yield:

methyl 2-acetamido-4-O-(3,4,6-tri-O-benzyl-β-L-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-L-glucopyranoside (652972-20-8) + 2,3,4-tri-O-benzyl-6-deoxy-D-galactose diethyl dithioacetal (692740-50-4) → methyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-β-D-fucopyranosyl)-β-L-galactopyranosyl]-β-L-glucopyranoside + methyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-β-L-galactopyranosyl]-β-L-glucopyranoside (692740-49-1)

Guidance literature:

With di-tert-butyl-4-methylpyridine; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; at 0 - 20 ℃; for 14h;

DOI:10.1021/jo035789l

Reference yield:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) → methyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-β-L-galactopyranosyl]-β-L-glucopyranoside (692740-49-1)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 85 percent / camphor sulfonic acid / tetrahydrofuran / 12 h / 85 °C

2.1: 82 percent / NaH / dimethylformamide / 48 h / 20 °C

3.1: 82 percent / lithium naphthalenide / tetrahydrofuran / -78 °C

4.1: dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / 0 °C

5.1: 80 percent / CuI / tetrahydrofuran / 0.33 h / -10 °C

6.1: 2.25 g / KOH; H₂O₂ / tetrahydrofuran; methanol / 18 h / 20 °C

7.1: (n-Bu)2SnO / toluene / 2 h / Heating

7.2: 94 percent / tetrabutylammonium iodide; triethylamine / toluene / 18 h / Heating

8.1: 96 percent / acetic acid / tetrahydrofuran; H₂O / 2 h / 45 °C

9.1: tetramethyl-1-piperidine oxide; NaClO; NaHCO₃ / CH₂Cl₂; H₂O / 0.5 h / 0 °C

10.1: 0.99 g / N,N-dimethylformamide dineopentyl acetate / xylene / 1 h / 75 - 150 °C

11.1: 73 percent / di-tert-butyl-4-methylpyridine; MeOTf / CH₂Cl₂; toluene / 18 h / 0 °C

12.1: 90 percent / I(sym-collidine)2ClO₄ / CH₂Cl₂ / 0.5 h / 0 °C

13.1: 95 percent / methanol / 18 h / 20 °C

14.1: 95 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 18 h / 20 °C

15.1: 81 percent / sodium naphthalenide / tetrahydrofuran / -78 °C

16.1: 99 percent / NaOMe / methanol / 18 h / 45 °C

17.1: dimethyl(methylthio)sulfonium triflate; di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 14 h / 0 - 20 °C

With dmap; potassium hydroxide; sodium hypochlorite; copper(l) iodide; di-tert-butyl-4-methylpyridine; iodonium(di-γ-collidine) perchlorate; tetramethyl-1-piperidine oxide; camphor-10-sulfonic acid; dihydrogen peroxide; sodium methylate; 3,3-dimethyldioxirane; sodium naphthalenide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine; naphthalen-1-yl-lithium; N,N-dimethylformamide dineopentyl acetal; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; xylene; 6.1: Tamao-Kumada oxidation;

DOI:10.1021/jo035789l

upstream raw materials:

methyl 2-acetamido-4-O-(3,4,6-tri-O-benzyl-β-L-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-L-glucopyranoside

ethyl 2,3,4-tri-O-benzyl-1-thio-D-fucopyranoside

2,3,4-tri-O-benzyl-6-deoxy-D-galactose diethyl dithioacetal

methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside