3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

Base Information

• Chemical Name: 3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose
• CAS No.: 879546-87-9
• Molecular Formula: C₁₈H₂₄O₆
• Molecular Weight: 336.385
• Mol file: 879546-87-9.mol

Synonyms:3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

Chemical Property of 3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

There total 3 articles about 3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose 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:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (3aR,5S,6R,6aR)-6-(benzyloxy)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde → 3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose (879546-87-9)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 18h;

DOI:10.1021/jo051187l

Reference yield:

(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol (96212-45-2) → 3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose (879546-87-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium periodate / tetrahydrofuran; H₂O / 0.75 h / 0 °C

2: 562 mg / sodium hydroxide / tetrahydrofuran; H₂O / 18 h / 20 °C

With sodium hydroxide; sodium periodate; In tetrahydrofuran; water; 2: aldol-Cannizzaro reaction;

DOI:10.1021/jo051187l

Reference yield:

(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole (96212-44-1) → 3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose (879546-87-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / aqueous acetic acid / 3 h / 40 °C

2: sodium periodate / tetrahydrofuran; H₂O / 0.75 h / 0 °C

3: 562 mg / sodium hydroxide / tetrahydrofuran; H₂O / 18 h / 20 °C

With sodium hydroxide; sodium periodate; acetic acid; In tetrahydrofuran; water; 3: aldol-Cannizzaro reaction;

DOI:10.1021/jo051187l

upstream raw materials:

formaldehyd

(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol

(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole

Downstream raw materials:

3,5-di-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

1-(3a-benzyloxy-7a-benzyloxymethyl-3-oxo-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

3,5-di-O-benzyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyloxymethyl)-3-C-vinyl-α-D-ribofuranose

1-((2R,3S,3aS,7aR)-3a-Benzyloxy-7a-benzyloxymethyl-3-hydroxy-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione