Methyl 3-acetamido-3,6-anhydro-4-O-benzoyl-2,3,6-trideoxy-α-D-arabino-hexopyranoside

Base Information

Chemical Name:Methyl 3-acetamido-3,6-anhydro-4-O-benzoyl-2,3,6-trideoxy-α-D-arabino-hexopyranoside
CAS No.:67693-28-1
Molecular Formula:C₁₆H₁₉NO₅
Molecular Weight:305.331
Hs Code.:

Synonyms:Methyl 3-acetamido-3,6-anhydro-4-O-benzoyl-2,3,6-trideoxy-α-D-arabino-hexopyranoside

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Chemical Property of Methyl 3-acetamido-3,6-anhydro-4-O-benzoyl-2,3,6-trideoxy-α-D-arabino-hexopyranoside

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Technology Process of Methyl 3-acetamido-3,6-anhydro-4-O-benzoyl-2,3,6-trideoxy-α-D-arabino-hexopyranoside

There total 7 articles about Methyl 3-acetamido-3,6-anhydro-4-O-benzoyl-2,3,6-trideoxy-α-D-arabino-hexopyranoside 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: 94.5%

: 63554-16-5
Methyl 3-acetamido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-α-D-arabino-hexopyranoside

: 67693-28-1
Methyl 3-acetamido-3,6-anhydro-4-O-benzoyl-2,3,6-trideoxy-α-D-arabino-hexopyranoside

Guidance literature:: With pyridine; silver fluoride; at 20 ℃; for 14h;
DOI:10.1055/s-2000-6328

Reference yield:

: 63598-31-2
methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose

: 67693-28-1
Methyl 3-acetamido-3,6-anhydro-4-O-benzoyl-2,3,6-trideoxy-α-D-arabino-hexopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: NaBH₄ / methanol / 2 h / 0 - 20 °C

2: pyridine / CH₂Cl₂ / 0.75 h / 20 °C

3: NaN₃ / dimethylformamide / 1.5 h / 20 °C

4: LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

5: pyridine / 2 h / 20 °C

6: 75.9 percent / NBS; BaCO₃ / CCl₄ / 6 h / Heating

7: 94.5 percent / AgF; pyridine / 14 h / 20 °C

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; sodium azide; silver fluoride; barium carbonate; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: Esterification / 3: Substitution / 4: Reduction / 5: Acetylation / 6: Substitution / 7: Cyclization;
DOI:10.1055/s-2000-6328

Reference yield:

: 102916-74-5
Methyl 3-azido-4,6-O-benzylidene-2,3-dideoxy-α-D-arabino-hexopyranoside

: 67693-28-1
Methyl 3-acetamido-3,6-anhydro-4-O-benzoyl-2,3,6-trideoxy-α-D-arabino-hexopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

2: pyridine / 2 h / 20 °C

3: 75.9 percent / NBS; BaCO₃ / CCl₄ / 6 h / Heating

4: 94.5 percent / AgF; pyridine / 14 h / 20 °C

With pyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; silver fluoride; barium carbonate; In tetrahydrofuran; tetrachloromethane; 1: Reduction / 2: Acetylation / 3: Substitution / 4: Cyclization;
DOI:10.1055/s-2000-6328