4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose

Base Information

• Chemical Name: 4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose
• CAS No.: 72261-44-0
• Molecular Formula: C16H22O6
• Molecular Weight: 310.347
• Mol file: 72261-44-0.mol

Synonyms:Furo[2,3-d]-1,3-dioxole,b-L-threo-pentofuranose deriv.;

Chemical Property of 4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose

Chemical Property:

• Vapor Pressure: 1.3E-08mmHg at 25°C
• Melting Point: 70-71 °C
• Refractive Index: 1.575
• Boiling Point: 442.5 °C at 760 mmHg
• PKA: 13.95±0.10(Predicted)
• Flash Point: 221.4 °C
• PSA: 77.38000
• Density: 1.29 g/cm³
• LogP: 0.80300
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose

There total 11 articles about 4-(Hydroxymethyl)-1,2-O-isopropylidene-3-O-benzyl-beta-L-threo-pentofuranose 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: 80.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (72261-44-0)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane;

Reference yield: 41.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (72261-44-0) + 1,2-O-isopropylidene-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (55797-64-3,55797-65-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 25 ℃; for 10h;

DOI:10.1016/j.tet.2004.03.034

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → 1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (72261-44-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 30.39 g / NaOH / dioxane; H₂O / 42 h / 20 °C

With sodium hydroxide; sodium periodate; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1016/j.bmc.2005.01.029

upstream raw materials:

formaldehyd

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

benzyl bromide

Downstream raw materials:

4-C-acetoxymethyl-5-O-acetyl-3-O-benzyl-1,2-O-(1-methylethylidene)-β-L-threo-pentofuranose

5-O-Benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-β-L-threo-pentofuranose

3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose

3-O-benzyl-5-(O-p-toluenesulfonyl)-4-C-(p-toluenesulfonyloxymethyl)-1,2-O-(isopropylidene)-β-L-threo-xylofuranose