(3,4,5-Triacetyloxy-6-benzylsulfanyloxan-2-yl)methyl acetate

Base Information

• Chemical Name: (3,4,5-Triacetyloxy-6-benzylsulfanyloxan-2-yl)methyl acetate
• CAS No.: 6612-63-1
• Molecular Formula: C21H26 O9 S
• Molecular Weight: 454.498
• NSC Number: 89880
• DSSTox Substance ID: DTXSID00293495
• Mol file: 6612-63-1.mol

Synonyms:6612-63-1;benzyl 2,3,4,6-tetra-o-acetyl-1-thiohexopyranoside;.BETA.-D-GLUCOPYRANOSIDE, PHENYLMETHYL 1-THIO-, TETRAACETATE;(3,4,5-triacetyloxy-6-benzylsulfanyloxan-2-yl)methyl acetate;NSC89880;DTXSID00293495;NSC-89880

Chemical Property of (3,4,5-Triacetyloxy-6-benzylsulfanyloxan-2-yl)methyl acetate

Chemical Property:

• Vapor Pressure: 3.73E-11mmHg at 25°C
• Boiling Point: 526°Cat760mmHg
• Flash Point: 252.6°C
• PSA: 139.73000
• Density: 1.29g/cm³
• LogP: 2.00290
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 454.12975358
• Heavy Atom Count: 31
• Complexity: 647

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)SCC2=CC=CC=C2)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of (3,4,5-Triacetyloxy-6-benzylsulfanyloxan-2-yl)methyl acetate

There total 24 articles about (3,4,5-Triacetyloxy-6-benzylsulfanyloxan-2-yl)methyl acetate 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: 97.0%

2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose (72541-16-3) + benzyl bromide (100-39-0) → benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (6612-63-1)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1021/jacs.6b08305

Reference yield: 90.0%

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide (40591-65-9) + benzyl chloride (100-44-7) → benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (6612-63-1)

Guidance literature:

With triethylamine; In acetonitrile; for 0.0333333h; microwave irradiation;

DOI:10.1080/00397910600767314

Reference yield: 88.0%

phenylmethanethiol (100-53-8) + β-D-glucose pentaacetate (604-69-3) → benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (6612-63-1)

Guidance literature:

With iodine; iron; In dichloromethane; at 20 ℃; for 6h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.07.077

upstream raw materials:

O²,O³,O⁴,O⁶-Tetraacetyl-1-thio-D-glucose

benzyl chloride

phenylmethanethiol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

2,3,4,5-tetra-O-acetyl-D-glucopyranose

phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,4,6-tri-O-benzyl-β-D-glucopyranoside

benzyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

(2R,3R,4S,5R)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-[1-phenyl-meth-(Z)-ylidene]-tetrahydro-pyran