phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside

Base Information

• Chemical Name: phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside
• CAS No.: 478687-09-1
• Molecular Formula: C₃₃H₃₄O₄S
• Molecular Weight: 526.697
• Mol file: 478687-09-1.mol

Synonyms:phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside

Chemical Property of phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside

There total 10 articles about phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside 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: 72.0%

phenyl 2,4,6-tri-O-benzyl-3-O-[(methylthio)thiocarbonyl]-1-thio-β-D-galactopyranoside → phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside (478687-09-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 3h; Reflux; Inert atmosphere;

DOI:10.1021/acs.orglett.8b02669

Reference yield: 70.0%

phenyl 2,3,6-tri-O-benzyl-4-O-phenoxythiocarbonyl-1-thio-β-D-glucopyranoside → phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside (478687-09-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmcl.2009.06.005

Reference yield:

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (87470-72-2) → phenyl 2,3,6-tri-O-benzyl-4-deoxy-1-thio-β-D-xylo-hexopyranoside (478687-09-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylsilane; trifluoroacetic acid / dichloromethane / 2 h / 0 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux

2.2: Inert atmosphere

3.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 3 h / Reflux; Inert atmosphere

With triethylsilane; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/acs.orglett.8b02669

upstream raw materials:

thiophenol

(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Downstream raw materials:

benzyl 2,4,6-tri-O-benzyl-3-deoxy-α-D-galactopyranosyl-(1,3)-2,4,6-tri-O-pivaloyl-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-pivaloyl-β-D-glucopyranoside

(2S,3R)-3-benzyloxy-2-(N-tert-butyloxycarbonylamino)-1-(2'',3'',6''-tri-O-benzyl-4''-deoxy-β-D-galactopyranosyl)octadecane

2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-N-acetyl-2,3,6-tri-O-acetyl-β-D-glucopyranosylamine

2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide