2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone
• CAS No.: 118206-39-6
• Molecular Formula: C₃₄H₃₄O₅S
• Molecular Weight: 554.707
• Mol file: 118206-39-6.mol

Synonyms:2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone

Chemical Property of 2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone

There total 7 articles about 2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone 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%

2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranose (72174-24-4) → 2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone (118206-39-6)

Guidance literature:

With tert-butylsulfinyl chloride; triethylamine; In toluene; at 20 - 110 ℃; for 0.333333h;

DOI:10.1016/j.tetlet.2008.05.145

Reference yield: 45.0%

1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-tert-butyl sulfinothioate → (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) + 2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone (118206-39-6)

Guidance literature:

In toluene; at 110 ℃; Inert atmosphere;

DOI:10.1039/c9ob01190k

Reference yield:

(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol (72174-24-4,53269-97-9) → (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) + 2,3,4,6-tetra-O-benzyl-D-glucono-δ-thionolactone (118206-39-6)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere

2: toluene / 110 °C / Inert atmosphere

With triethylamine; In toluene;

DOI:10.1039/c9ob01190k

upstream raw materials:

methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide

(2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-methyldisulfanyl-tetrahydro-pyran

2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranose

O-ethyl S-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl) dithiocarbonate

Downstream raw materials:

(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(3-methyl-indol-1-yl)-tetrahydro-pyran-2-thiol