4-NITROPHENYL HEPTA-O-ACETYL-1-THIO-BETA

Base Information

• Chemical Name: 4-NITROPHENYL HEPTA-O-ACETYL-1-THIO-BETA
• CAS No.: 78006-49-2
• Molecular Formula: C₃₂H₃₉NO₁₉S
• Molecular Weight: 773.723
• Mol file: 78006-49-2.mol

Synonyms:4-NITROPHENYL HEPTA-O-ACETYL-1-THIO-BETA;4-Nitrophenyl 4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-1-thio-alpha-D-glucopyranoside 2,3,6-triacetate

Chemical Property of 4-NITROPHENYL HEPTA-O-ACETYL-1-THIO-BETA

Chemical Property:

• PSA: 282.91000
• LogP: 1.82980
• Storage Temp.: −20°C

Purity/Quality:

97% ^*data from raw suppliers

4-Nitrophenyl hepta-O-acetyl-1-thio-b-lactoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-NITROPHENYL HEPTA-O-ACETYL-1-THIO-BETA

There total 2 articles about 4-NITROPHENYL HEPTA-O-ACETYL-1-THIO-BETA 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: 60.0%

sodium 4-nitrobenzenethiolate (13113-79-6) + 2,3,6-tri-O-acetyl-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl chloride (7166-81-6) → Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-nitro-phenylsulfanyl)-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (78006-49-2)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide; 40 deg C, 6 h; r.t.;

Reference yield:

1,2,3,6,2',3',4',6'-octa-O-acetylmaltose (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4,20880-60-8) → Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-nitro-phenylsulfanyl)-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (78006-49-2)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethyl methyl ether, boron trifluoride

2: 60 percent / hexamethylphosphoric acid triamide / 40 deg C, 6 h; r.t.

With Dichloromethyl methyl ether; boron trifluoride; In N,N,N,N,N,N-hexamethylphosphoric triamide;

Reference yield:

Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-nitro-phenylsulfanyl)-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (78006-49-2) → (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenylsulfanyl)-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (77988-26-2)

Guidance literature:

With sodium methylate; In methanol; Yield given;

upstream raw materials:

sodium 4-nitrobenzenethiolate

2,3,6-tri-O-acetyl-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl chloride

1,2,3,6,2',3',4',6'-octa-O-acetylmaltose

Downstream raw materials:

(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenylsulfanyl)-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Refernces