[(4aR,6S,7R,8S,8aR)-6-methoxy-7-(4-methylphenyl)sulfonyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 4-methylbenzenesulfonate

Base Information

• Chemical Name: [(4aR,6S,7R,8S,8aR)-6-methoxy-7-(4-methylphenyl)sulfonyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 4-methylbenzenesulfonate
• CAS No.: 6884-01-1
• Molecular Formula: C28H30O10S2
• Molecular Weight: 590.672
• European Community (EC) Number: 229-987-8
• Nikkaji Number: J265.940I
• Mol file: 6884-01-1.mol

Synonyms:6884-01-1;Methyl 4,6-O-benzylidene-2,3-di-O-p-toluenesulfonyl-a-D-glucopyranoside;[(4aR,6S,7R,8S,8aR)-6-methoxy-7-(4-methylphenyl)sulfonyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 4-methylbenzenesulfonate;METHYL 4,6-O-BENZYLIDENE-2,3-DI-O-(TOSYL)-ALPHA-D-GLUCOPYRANOSIDE;70774-92-4;Methyl 4,6-O-benzylidene-2,3-di-O-(p-toluenesulfonyl)-a-D-glucopyranoside;SCHEMBL5519961;EINECS 229-987-8;NSC 89882;A1-00775;Methyl 2-O,3-O-ditosyl-4-O,6-O-benzylidene-alpha-D-glucopyranoside;4,6-O-Benzylidene-alpha-D-glucopyranoside methyl bis(4-methylbenzenesulphonate);Methyl 4,6-O-benzylidene-2,3-di-O-p-toluenesulfonyl-alpha-D-glucopyranoside

Chemical Property of [(4aR,6S,7R,8S,8aR)-6-methoxy-7-(4-methylphenyl)sulfonyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 4-methylbenzenesulfonate

Chemical Property:

• Boiling Point: 737.8oC at 760 mmHg
• Flash Point: 400oC
• PSA: 140.42000
• Density: 1.43g/cm3
• LogP: 5.79850
• Storage Temp.: -20°C Freezer
• Solubility.: Dichloromethane; Methanol
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 590.12803950
• Heavy Atom Count: 40
• Complexity: 1020

Purity/Quality:

Methyl 4,6-O-benzylidene-2,3-di-O-(p-toluenesulfonyl)-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC2C3C(COC(O3)C4=CC=CC=C4)OC(C2OS(=O)(=O)C5=CC=C(C=C5)C)OC
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O[C@H]2[C@H]3[C@@H](COC(O3)C4=CC=CC=C4)O[C@@H]([C@@H]2OS(=O)(=O)C5=CC=C(C=C5)C)OC
• Uses: Methyl 4,6-O-Benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside is an intermediate in the synthesis of Digoxigenin Tetradigitoxoside (D446510), a Digoxin (Dx) (D446575) impurity.

Technology Process of [(4aR,6S,7R,8S,8aR)-6-methoxy-7-(4-methylphenyl)sulfonyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 4-methylbenzenesulfonate

There total 18 articles about [(4aR,6S,7R,8S,8aR)-6-methoxy-7-(4-methylphenyl)sulfonyloxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 4-methylbenzenesulfonate 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: 92.2%

(+)-4,6-benzylidene-α-D-glucopyranoside (3162-96-7) + p-toluenesulfonyl chloride (98-59-9) → methyl 4,6-O-benzylidene-2,3-di-O-p-toluenesulphonyl-α-D-glucopyranoside (6884-01-1)

Guidance literature:

With pyridine; at 80 ℃; for 48h;

DOI:10.1021/jo00265a033

Reference yield: 87.0%

benzaldehyde dimethyl acetal (1125-88-8) + p-toluenesulfonyl chloride (98-59-9) + methyl beta-D-galactopyranoside (1824-94-8) → methyl 4,6-O-benzylidene-β-D-galactopyranoside 2,3-di-O-p-toluenesulfonate (6748-86-3,6884-01-1,6988-45-0,15384-63-1,30010-02-7,32976-12-8,32976-13-9,65530-22-5,65530-24-7,65530-25-8,65556-00-5,69651-81-6,86420-66-8,86420-75-9,99265-93-7,99265-97-1,103772-99-2)

Guidance literature:

benzaldehyde dimethyl acetal; methyl beta-D-galactopyranoside; With camphor-10-sulfonic acid; In N,N-dimethyl-formamide;

p-toluenesulfonyl chloride; With pyridine;

DOI:10.1021/jo300764k

Reference yield: 83.0%

p-toluenesulfonyl chloride (98-59-9) + methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside (71117-36-7) → methyl 4,6-O-benzylidene-β-D-galactopyranoside 2,3-di-O-p-toluenesulfonate (6748-86-3,6884-01-1,6988-45-0,15384-63-1,30010-02-7,32976-12-8,32976-13-9,65530-22-5,65530-24-7,65530-25-8,65556-00-5,69651-81-6,86420-66-8,86420-75-9,99265-93-7,99265-97-1,103772-99-2) + methyl 4,6-O-benzylidene-β-D-galactopyranoside 2-O-p-toluenesulfonate (86420-69-1) + methyl 4,6-O-benzylidene-β-D-galactopyranoside 3-O-p-toluenesulfonate (86470-08-8)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In dichloromethane; for 1.5h;

upstream raw materials:

p-toluenesulfonyl chloride

methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside

methyl beta-D-galactopyranoside

benzaldehyde dimethyl acetal

Downstream raw materials:

methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside

methyl 4,6-O-benzylidene-2,3-dideoxy-β-D-threo-hex-2-enoside

(4R,5R)-4,6-dibenzyloxy-5-hydroxyhexanal ethylene dithioacetal

(4R,5S)-5-azido-4,6-dibenzyloxyhexanal