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

Base Information

Chemical Name:methyl 3-azido-3-deoxy-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside
CAS No.:157068-63-8
Molecular Formula:C₁₅H₂₁N₃O₅
Molecular Weight:323.349
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 9 articles about methyl 3-azido-3-deoxy-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: 85.0%

: 100-39-0
benzyl bromide

: 157068-62-7
(2R,3R,4R,5R,6R)-4-Azido-2-hydroxymethyl-5,6-dimethoxy-tetrahydro-pyran-3-ol

: 157068-63-8
methyl 3-azido-3-deoxy-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside

Guidance literature:: With 3 A molecular sieve; tetrabutylammomium bromide; di(n-butyl)tin oxide; In acetonitrile; at 80 ℃; for 8h;
DOI:10.1021/jo00096a022

Reference yield:

: 35780-85-9
methyl 2-O-methyl-4,6-O-(phenylmethylene)-β-D-galactopyranoside

: 157068-63-8
methyl 3-azido-3-deoxy-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside

Guidance literature:: Multi-step reaction with 4 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

With pyridine; 3 A molecular sieve; tetrabutylammomium bromide; di(n-butyl)tin oxide; trifluoroacetic acid; In methanol; dichloromethane; acetonitrile; benzene;
DOI:10.1021/jo00096a022

Reference yield:

: 104530-15-6
methyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-β-D-galactopyranoside

: 157068-63-8
methyl 3-azido-3-deoxy-2-O-methyl-6-O-(phenylmethyl)-β-D-gulopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: NaH / tetrahydrofuran / 4 h

2: pyridinium p-toluenesulfonate / methanol / 2 h

3: p-toluenesulfonic acid / methanol / 4 h

4: CH₂Cl₂ / 1.5 h

5: pyridine / CH₂Cl₂ / 20 h / 0 °C

6: benzene / 24 h / 23 °C

7: 97 percent / CF₃COOH / methanol / 22 h / 45 °C

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

With pyridine; 3 A molecular sieve; tetrabutylammomium bromide; pyridinium p-toluenesulfonate; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; benzene;
DOI:10.1021/jo00096a022