2C-Hydroxymethyl-2,3:5,6-di-O-isopropylidene-L-gulono-1,4-lactone

Base Information

• Chemical Name: 2C-Hydroxymethyl-2,3:5,6-di-O-isopropylidene-L-gulono-1,4-lactone
• CAS No.: 64487-91-8
• Molecular Formula: C13H20 O7
• Molecular Weight: 288.29
• Mol file: 64487-91-8.mol

Synonyms:Furo[3,4-d]-1,3-dioxole,L-gulonic acid deriv.

Chemical Property of 2C-Hydroxymethyl-2,3:5,6-di-O-isopropylidene-L-gulono-1,4-lactone

Chemical Property:

• PSA: 83.45000
• LogP: -0.05410

Purity/Quality:

95% ^*data from raw suppliers

2C-Hydroxymethyl-2,3:5,6-di-O-isopropylidene-L-gulono-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2C-Hydroxymethyl-2,3:5,6-di-O-isopropylidene-L-gulono-1,4-lactone

There total 6 articles about 2C-Hydroxymethyl-2,3:5,6-di-O-isopropylidene-L-gulono-1,4-lactone 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: 96.0%

(3aS,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-ol (91738-34-0,91738-35-1) → 2-C-hydroxymethyl-2,3:5,6-di-O-isopropylidene-L-gulono-1,4-lactone (64487-91-8)

Guidance literature:

With bromine; barium carbonate; In 1,4-dioxane;

DOI:10.1016/j.tetlet.2004.10.086

Reference yield: 17.0%

L-sorbose (87-79-6,18875-34-8) + sodium cyanide (143-33-9,25596-52-5) + acetone (67-64-1) → (8S,9S)-8-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-9-hydroxy-2,2-dimethyl-1,3,7-trioxa-spiro[4.4]nonan-6-one + 2-C-hydroxymethyl-2,3:5,6-di-O-isopropylidene-L-gulono-1,4-lactone (64487-91-8)

Guidance literature:

L-sorbose; sodium cyanide; With water; Heating;

acetone; With copper(I) sulfate; sulfuric acid; copper(II) sulfate; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2004.10.086

Reference yield:

2,3:5,6-di-O-isopropylidene-L-gulonolactone (7306-64-1) → 2-C-hydroxymethyl-2,3:5,6-di-O-isopropylidene-L-gulono-1,4-lactone (64487-91-8)

Guidance literature:

Multi-step reaction with 3 steps

1: diisobutylaluminum hydride / tetrahydrofuran

2: 70 percent / aq. K₂CO₃

3: 96 percent / aq. bromine; barium carbonate / dioxane

With bromine; diisobutylaluminium hydride; potassium carbonate; barium carbonate; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/j.tetlet.2004.10.086

upstream raw materials:

(3aS,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-ol

L-sorbose

sodium cyanide

acetone

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