pentachlorophenyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: pentachlorophenyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS No.: 110519-31-8
• Molecular Formula: C₄₄H₅₁Cl₅O₂₆
• Molecular Weight: 1173.14
• Mol file: 110519-31-8.mol

Synonyms:

Chemical Property of pentachlorophenyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pentachlorophenyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

There total 4 articles about pentachlorophenyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-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:

Pentachlorophenol (87-86-5,67471-28-7) + Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-((2R,3R,4S,5R)-4,5-diacetoxy-2-acetoxymethyl-6-bromo-tetrahydro-pyran-3-yloxy)-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (76821-27-7) → pentachlorophenyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (110519-31-8)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In ethyl acetate; at 20 ℃; for 18h;

DOI:10.1055/s-2002-20038

Reference yield:

maltotriose peracetate (76821-26-6) → pentachlorophenyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (110519-31-8)

Guidance literature:

Multi-step reaction with 2 steps

1: HBr; AcOH / CH₂Cl₂ / 5 h / 10 - 15 °C

2: 9.18 g / tetrabutylammonium hydrogen sulfate; aq. Na₂CO₃ / ethyl acetate / 18 h / 20 °C

With hydrogen bromide; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; acetic acid; In dichloromethane; ethyl acetate;

DOI:10.1055/s-2002-20038

Reference yield:

sodium pentachlorphenate (131-52-2) + (2S,3R,4S,5R,6R)-6-(acetoxymethyl)-5-((2R,3R,4S,5R,6R)-3,4-diacetoxy-6-(acetoxymethyl)-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2,3,4-triyl triacetate (17690-94-7,31873-40-2,31873-41-3,35396-13-5,54192-78-8,61139-07-9,61687-84-1,61687-85-2,69349-75-3,76821-26-6,80446-83-9,113473-58-8,116182-08-2,139894-77-2,141847-33-8,151061-59-5,151061-60-8) → pentachlorophenyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-O-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (110519-31-8)

Guidance literature:

With hydrogen bromide; Yield given. Multistep reaction; 1.) AcOH, 15-20 deg C, 3 h, 2.) acetone, reflux, overnight;

DOI:10.1016/0008-6215(89)84024-8

upstream raw materials:

sodium pentachlorphenate

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

acetic anhydride

Pentachlorophenol

Downstream raw materials:

(4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-[(2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((1R,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-[(2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((1R,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-3-yloxy]-2-iodomethyl-tetrahydro-pyran-3-ol

1¹,6¹-anhydro-2¹,3¹,2²,3²,6²,2³,3³-hepta-O-benzyl-β-maltotriose

(2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-[(2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((1R,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-ylamine