methyl 3-O-allyl-2-O-[2',3',4'-tri-O-benzyl-6'-O-(6''-trityloxyhexyl)-α-D-galactopyranosyl]-4-O-benzyl-6-O-methanesulfonyl-α-D-mannopyranoside

Base Information

Chemical Name:methyl 3-O-allyl-2-O-[2',3',4'-tri-O-benzyl-6'-O-(6''-trityloxyhexyl)-α-D-galactopyranosyl]-4-O-benzyl-6-O-methanesulfonyl-α-D-mannopyranoside
CAS No.:213767-49-8
Molecular Formula:C₇₀H₈₀O₁₄S
Molecular Weight:1177.46
Hs Code.:

Synonyms:methyl 3-O-allyl-2-O-[2',3',4'-tri-O-benzyl-6'-O-(6''-trityloxyhexyl)-α-D-galactopyranosyl]-4-O-benzyl-6-O-methanesulfonyl-α-D-mannopyranoside

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Chemical Property of methyl 3-O-allyl-2-O-[2',3',4'-tri-O-benzyl-6'-O-(6''-trityloxyhexyl)-α-D-galactopyranosyl]-4-O-benzyl-6-O-methanesulfonyl-α-D-mannopyranoside

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Technology Process of methyl 3-O-allyl-2-O-[2',3',4'-tri-O-benzyl-6'-O-(6''-trityloxyhexyl)-α-D-galactopyranosyl]-4-O-benzyl-6-O-methanesulfonyl-α-D-mannopyranoside

There total 17 articles about methyl 3-O-allyl-2-O-[2',3',4'-tri-O-benzyl-6'-O-(6''-trityloxyhexyl)-α-D-galactopyranosyl]-4-O-benzyl-6-O-methanesulfonyl-α-D-mannopyranoside 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: 77.0%

: 213766-15-5
methyl 3-O-allyl-4-O-benzyl-6-O-methanesulfonyl-α-D-mannopyranoside

: 213766-20-2
ethyl 2,3,4-tri-O-benzyl-6-O-(6'-trityloxyhexyl)-1-thio-α-D-galactopyranoside

: 213767-49-8
methyl 3-O-allyl-2-O-[2',3',4'-tri-O-benzyl-6'-O-(6''-trityloxyhexyl)-α-D-galactopyranosyl]-4-O-benzyl-6-O-methanesulfonyl-α-D-mannopyranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; Ambient temperature;
DOI:10.1021/jo9806097

Reference yield:

: 100-39-0
benzyl bromide

: 213767-49-8
methyl 3-O-allyl-2-O-[2',3',4'-tri-O-benzyl-6'-O-(6''-trityloxyhexyl)-α-D-galactopyranosyl]-4-O-benzyl-6-O-methanesulfonyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 84 percent / NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) o deg C to room temperature

2: 84 percent / 80percent AcOH / 4 h / 80 °C

3: 1.) dibutyltin oxide, 2.) tetrabutylammonium iodide / 1.) MeOH, reflux, 2.5 h, 2.) toluene, 60 deg C, 15 h

4: 84 percent / pyridine / Ambient temperature

5: 84 percent / TBAF / tetrahydrofuran / 6 h / Ambient temperature

6: 88 percent / pyridine / Ambient temperature

7: 95 percent / Na / methanol

8: 77 percent / NIS, TfOH / CH₂Cl₂ / Ambient temperature

With N-iodo-succinimide; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; acetic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo9806097

Reference yield:

: 629-11-8
1,6-hexanediol

: 213767-49-8
methyl 3-O-allyl-2-O-[2',3',4'-tri-O-benzyl-6'-O-(6''-trityloxyhexyl)-α-D-galactopyranosyl]-4-O-benzyl-6-O-methanesulfonyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 52 percent / pyridine; CH₂Cl₂ / Ambient temperature

2: 81 percent / pyridine; CH₂Cl₂ / Ambient temperature

3: 98 percent / NaH / tetrahydrofuran / 1.) 50 deg C, 1 h, 2.) 65 deg C, 18 h

4: 77 percent / NIS, TfOH / CH₂Cl₂ / Ambient temperature

With N-iodo-succinimide; trifluorormethanesulfonic acid; sodium hydride; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1021/jo9806097