levoglucosan tritosylate

Base Information

• Chemical Name: levoglucosan tritosylate
• CAS No.: 50880-93-8
• Molecular Formula: C₂₇H₂₈O₁₁S₃
• Molecular Weight: 624.711
• Mol file: 50880-93-8.mol

Synonyms:levoglucosan tritosylate

Chemical Property of levoglucosan tritosylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of levoglucosan tritosylate

There total 9 articles about levoglucosan tritosylate 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: 85.0%

p-toluenesulfonyl chloride (98-59-9) + levoglucosan (498-07-7) → [(1R,2S,3S,4R,5R)-3-hydroxy-4-(p-tolylsulfonyl)-6,8-dioxabicyclo[3.2.1]oct-2-yl]-4-methylbenzenesulfonic acid (20204-80-2) + levoglucosan tritosylate (50880-93-8)

Guidance literature:

With pyridine; at -5 ℃; for 12.5h;

DOI:10.1021/jo991719w

Reference yield: 28.0%

p-toluenesulfonyl chloride (98-59-9) + levoglucosan (498-07-7) → 1,6-anhydro-2-O-(4-toluenesulfonyl)-β-D-glucopyranose (3868-05-1) + 1,6-anhydro-4-O-(4-toluenesulfonyl)-β-D-glucopyranose (23643-29-0) + [(1R,2S,3S,4R,5R)-3-hydroxy-4-(p-tolylsulfonyl)-6,8-dioxabicyclo[3.2.1]oct-2-yl]-4-methylbenzenesulfonic acid (20204-80-2) + levoglucosan tritosylate (50880-93-8)

Guidance literature:

With pyridine; In acetone;

Reference yield:

D-Allose (2595-97-3) → tris-O-(toluene-4-sulfonyl)-1,6-anhydro-β-D-allopyranose (50880-93-8)

Guidance literature:

Multi-step reaction with 2 steps

1: aqueous hydrochloric acid

2: pyridine

With pyridine; hydrogenchloride;

DOI:10.1021/ja01612a062

upstream raw materials:

p-toluenesulfonyl chloride

1,6-anhydro-β-D-glucopyranoside

D-Allose

1,6-Anhydro-β-D-gulopyranose

Downstream raw materials:

1,6:3,4-dianhydro-2-O-tosyl-D-galactose

1,6-anhydro-3,4-dideoxy-D-threo-hexopyranoside and 1,6-anhydro-3,4-dideoxy-D-threo-hexopyranoside

(1R,3S,5S)-6,8-dioxabicyclo[3.2.1]octan-3-ol

Acetic acid (3R,4S,5R,6R)-6-acetoxymethyl-3,4,5-tris-(toluene-4-sulfonyloxy)-tetrahydro-pyran-2-yl ester