Phenyl 4,6-O-Benzylidene-1-thio-beta-D-glucopyranoside

Base Information

• Chemical Name: Phenyl 4,6-O-Benzylidene-1-thio-beta-D-glucopyranoside
• CAS No.: 87508-17-6
• Molecular Formula: C₁₉H₂₀O₅S
• Molecular Weight: 360.431
• DSSTox Substance ID: DTXSID60431331
• Nikkaji Number: J937.396I
• Wikidata: Q82245185
• Mol file: 87508-17-6.mol

Synonyms:87508-17-6;Phenyl 4,6-O-Benzylidene-1-thio-beta-D-glucopyranoside;(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-(phenylthio)hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol;(2R,4aR,6S,7R,8R,8aS)-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol;SCHEMBL12347309;DTXSID60431331;AKOS030524318;AS-71002;CS-0226060;A847934;Phenyl 4,6-O-Benzylidene-1-thio-|A-D-glucopyranoside;Phenyl 4-O,6-O-[(R)-benzylidene]-1-thio-beta-D-glucopyranoside;(2R,4AR,6S,7R,8R,8AS)-2-PHENYL-6-(PHENYLSULFANYL)-HEXAHYDRO-2H-PYRANO[3,2-D][1,3]DIOXINE-7,8-DIOL

Chemical Property of Phenyl 4,6-O-Benzylidene-1-thio-beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 185 °C
• Refractive Index: -45.5 ° (C=1, CHCl3)
• Boiling Point: 581.153 °C at 760 mmHg
• Flash Point: 305.271 °C
• PSA: 93.45000
• Density: 1.397 g/cm³
• LogP: 2.33960
• Storage Temp.: Freezer
• Solubility.: slightly sol. in Chloroform
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 360.10314491
• Heavy Atom Count: 25
• Complexity: 424

Purity/Quality:

98%, ^*data from raw suppliers

Phenyl 4,6-O-Benzylidene-1-thio-β-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(C(C(C(O2)SC3=CC=CC=C3)O)O)OC(O1)C4=CC=CC=C4
• Isomeric SMILES: C1[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)SC3=CC=CC=C3)O)O)O[C@@H](O1)C4=CC=CC=C4
• Uses: This is a protected glucopyranoside useful as a building block for synthesis of complex carbohydrates. The compound has β-phenylthio and 4,6-benzylidene protecting groups.

Technology Process of Phenyl 4,6-O-Benzylidene-1-thio-beta-D-glucopyranoside

There total 38 articles about Phenyl 4,6-O-Benzylidene-1-thio-beta-D-glucopyranoside 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: 100.0%

benzaldehyde dimethyl acetal (1125-88-8) + (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) → (2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (71676-30-7,87508-18-7,138922-03-9,87508-17-6)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 60 ℃; pH=2 - 3; Inert atmosphere;

DOI:10.1080/10286020.2011.653348

Reference yield: 95.0%

phenyl 2-O-acetyl-3-O-(azulen-1-yl-oxo-acetyl)-4,6-O-benzylidene-β-D-thiogalactopyranoside (1203546-87-5) → phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside (71676-30-7,87508-17-6,138922-03-9,87508-18-7)

Guidance literature:

With methanol; sodium methylate; pH=9.5;

DOI:10.1016/j.tetlet.2009.10.043

Reference yield: 92.0%

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose (13992-16-0,23661-28-1,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1,24404-53-3) + benzaldehyde dimethyl acetal (1125-88-8) → phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside (71676-30-7,87508-17-6,138922-03-9,87508-18-7)

Guidance literature:

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose; With sodium methylate; In methanol; at 20 ℃; for 16h;

benzaldehyde dimethyl acetal; With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 40 ℃; for 23h;

DOI:10.1016/j.bmc.2016.06.007

upstream raw materials:

1-thiophenyl-β-D-galactopyranoside

benzaldehyde

benzaldehyde dimethyl acetal

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose

Downstream raw materials:

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

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

Dithiocarbonic acid O-((2S,4aR,6S,7R,8S,8aS)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl) ester S-methyl ester

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

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