tris(thiophenyl) 3-O-benzyl-1,2-O-isopropylidene-β-L-orthoidofuranuronate

Base Information

• Chemical Name: tris(thiophenyl) 3-O-benzyl-1,2-O-isopropylidene-β-L-orthoidofuranuronate
• CAS No.: 262382-45-6
• Molecular Formula: C₃₄H₃₄O₅S₃
• Molecular Weight: 618.839
• Mol file: 262382-45-6.mol

Synonyms:tris(thiophenyl) 3-O-benzyl-1,2-O-isopropylidene-β-L-orthoidofuranuronate

Chemical Property of tris(thiophenyl) 3-O-benzyl-1,2-O-isopropylidene-β-L-orthoidofuranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tris(thiophenyl) 3-O-benzyl-1,2-O-isopropylidene-β-L-orthoidofuranuronate

There total 7 articles about tris(thiophenyl) 3-O-benzyl-1,2-O-isopropylidene-β-L-orthoidofuranuronate 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: 92.0%

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → tris(thiophenyl) 3-O-benzyl-1,2-O-isopropylidene-β-L-orthoidofuranuronate (262382-45-6)

Guidance literature:

tris(phenylthio)methane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h;

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 17h;

Reference yield: 92.0%

tris(phenylthio)methane (4832-52-4) + 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → tris(thiophenyl) 3-O-benzyl-1,2-O-isopropylidene-β-L-orthoidofuranuronate (262382-45-6)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(99)02080-8

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → tris(thiophenyl) 3-O-benzyl-1,2-O-isopropylidene-β-L-orthoidofuranuronate (262382-45-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH; tetrabutylammonium iodide / tetrahydrofuran / 14 h / 20 °C

2.1: 17.8 g / acetic acid / H₂O / 16 h / 20 °C

3.1: sodium periodate; silica gel / CH₂Cl₂; H₂O / 1.5 h

4.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - -50 °C

4.2: tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C

With sodium periodate; n-butyllithium; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1021/jo0340760

upstream raw materials:

tris(phenylthio)methane

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:

methyl 3-O-benzyl-L-idopyranosyluronate

1,2-O-isopropylidene-3-O-benzyl-4-O-trichloroacetyl-6-methyl-α-L-idonic acid

methyl 4-O-allyl-3-O-benzyl-1,2-O-isopropylidene-α-L-idopyranosiduronate

methyl 3,4-di-O-benzyl-1,2-O-isopropylidene-α-L-idopyranosiduronate

Refernces

• 1、 -. "Compounds that bind to the interferon-gamma, preparation method thereof and medicaments containing same". Page/Page column 21. . Retrieved 2008/06/13.
• 2、 Lohman, Gregory J. S.,Hunt, Diana K.,H?germeier, Jens A.,Seeberger, Peter H.. "Synthesis of iduronic acid building blocks for the modular assembly of glycosaminoglycans". . p. 7559 - 7561. Retrieved 2007/10/03.