methyl 3-azido-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside

Base Information

• Chemical Name: methyl 3-azido-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside
• CAS No.: 157068-64-9
• Molecular Formula: C₃₅H₄₅F₃N₄O₁₀
• Molecular Weight: 738.758

Synonyms:methyl 3-azido-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside

Chemical Property of methyl 3-azido-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside

Chemical Property:

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Technology Process of methyl 3-azido-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside

There total 15 articles about methyl 3-azido-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside 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: 90.0%

methyl 3-azido-3-deoxy-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside (157068-63-8) + phenyl 3,4-dideoxy-2-O-(2,2-dimethylpropionyl)-6-O-(phenylmethyl)-1-thio-3-trifluoroacetamido-β-D-glucopyranoside (157068-61-6) → methyl 3-azido-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside (157068-64-9)

Guidance literature:

With N-iodo-succinimide; 3 A molecular sieve; In dichloromethane; for 0.166667h;

DOI:10.1021/jo00096a022

Reference yield:

methyl 2-O-methyl-4,6-O-(phenylmethylene)-β-D-galactopyranoside (35780-85-9) → methyl 3-azido-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside (157068-64-9)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / CH₂Cl₂ / 20 h / 0 °C

2: benzene / 24 h / 23 °C

3: 97 percent / CF₃COOH / methanol / 22 h / 45 °C

4: 85 percent / di-n-butyltin oxide, tetra-n-butylammonium bromide, 3 Angstroem molecular sieves / acetonitrile / 8 h / 80 °C

5: 90 percent / 3 Angstroem molecular sieves, N-iodosuccinimide / CH₂Cl₂ / 0.17 h

With pyridine; N-iodo-succinimide; 3 A molecular sieve; tetrabutylammomium bromide; di(n-butyl)tin oxide; trifluoroacetic acid; In methanol; dichloromethane; acetonitrile; benzene;

DOI:10.1021/jo00096a022

Reference yield:

benzyl bromide (100-39-0) → methyl 3-azido-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside (157068-64-9)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / tetrahydrofuran / 3 h

2: tetrahydrofuran / 1 h

3: H₂O / tetrahydrofuran / 2 h

4: Et₃N / CH₂Cl₂ / 0.5 h

5: 90 percent / 3 Angstroem molecular sieves, N-iodosuccinimide / CH₂Cl₂ / 0.17 h

With N-iodo-succinimide; 3 A molecular sieve; water; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00096a022

upstream raw materials:

methyl 3-azido-3-deoxy-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside

phenyl 3,4-dideoxy-2-O-(2,2-dimethylpropionyl)-6-O-(phenylmethyl)-1-thio-3-trifluoroacetamido-β-D-glucopyranoside

methyl 2-O-methyl-4,6-O-(phenylmethylene)-β-D-galactopyranoside

benzyl bromide

Downstream raw materials:

methyl 3-amino-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-3-N-<(trichloroacetamido)carbonyl>-β-D-gulopyranoside

2,2-Dimethyl-propionic acid (2S,3R,4S,6S)-2-((2R,3R,4R,5R,6R)-4-amino-2-benzyloxymethyl-5,6-dimethoxy-tetrahydro-pyran-3-yloxy)-6-benzyloxymethyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

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