1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside

Base Information

• Chemical Name: 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside
• CAS No.: 245432-69-3
• Molecular Formula: C₁₈H₂₂O₈
• Molecular Weight: 366.368
• Mol file: 245432-69-3.mol

Synonyms:1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside

Chemical Property of 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside

There total 11 articles about 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside 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: 79.0%

acetic anhydride (108-24-7) + benzyl (3-C-benzyloxymethyl)-2,3-O-isopropylidene-β-D-erythrofuranoside → 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside (245432-69-3)

Guidance literature:

benzyl (3-C-benzyloxymethyl)-2,3-O-isopropylidene-β-D-erythrofuranoside; With formic acid; at 60 ℃;

acetic anhydride; With pyridine; dmap; at 20 ℃;

DOI:10.1016/S0040-4020(99)00527-X

Reference yield: 79.0%

acetic anhydride (108-24-7) + (3aR,6R,6aR)-3a-Benzyloxymethyl-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole → 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside (245432-69-3)

Guidance literature:

With pyridine; formic acid; at 60 ℃;

DOI:10.1039/c1ob05587a

Reference yield:

methyl 2,3-O-isopropylidene-3-C-(hydroxymethyl)-α-D-erythrofuranoside (24679-88-7) → 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside (245432-69-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 82 percent / NaH / dimethylformamide / 20 °C

2.1: aq. HCOOH / 60 °C

2.2: DMAP; pyridine / 20 °C

With formic acid; sodium hydride; In N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: Hydrolysis / 2.2: Acetylation;

DOI:10.1016/S0040-4020(99)00527-X

upstream raw materials:

acetic anhydride

methyl 2,3-O-isopropylidene-3-C-(hydroxymethyl)-α-D-erythrofuranoside

1,2:3,5-di-O-isopropylidene-α-D-threo-apiofuranose

3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside

Downstream raw materials:

C₁₉H₂₄N₃O₈P

1'-(thymin-1-yl)-2',3'-(dideoxydidehydro)-5'-(O-benzyl)-β-D-apio-D-furanose

1'-(adenin-9-yl)-2',3'-(O-thiocarbonyl)-5'-(O-benzyl)-β-D-apio-D-furanose

1'-(thymin-1-yl)-2',3'-(O-thiocarbonyl)-5'-(O-benzyl)-β-D-apio-D-furanose