O-(2,6-Di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose

Base Information

• Chemical Name: O-(2,6-Di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose
• CAS No.: 126660-00-2
• Molecular Formula: C₃₂H₄₂O₁₆
• Molecular Weight: 682.676
• Mol file: 126660-00-2.mol

Synonyms:O-(2,6-Di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose

Chemical Property of O-(2,6-Di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2,6-Di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose

There total 3 articles about O-(2,6-Di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose 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: 75.0%

O-(2,6-Di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl bromide (126659-99-2) + benzyl alcohol (100-51-6,185532-71-2) → O-(2,6-Di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose (126660-00-2)

Guidance literature:

With tetrabutylammomium bromide; triethylamine; In dichloromethane; at 60 ℃; for 16h;

DOI:10.1016/0008-6215(90)80018-X

Reference yield:

Allyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside (103136-46-5) → O-(2,6-Di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose (126660-00-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) (Ph₃P)3Rh(I)Cl, diazabicyclo<2.2.2>octane 2) HgCl₂, HgO / 1) EtOH, PhH, H₂O, 20h, reflux 2) Me₂CO, H₂O, 1h, 20 deg C

2: 60 percent / CBr₄, (Me₂N)3P, TMSOTf / CH₂Cl₂ / 16 h / 25 °C

3: 75 percent / Bu₄NBr, Et₃N / CH₂Cl₂ / 16 h / 60 °C

With 1,4-diaza-bicyclo[2.2.2]octane; Wilkinson's catalyst; carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; triethylamine; mercury dichloride; mercury(II) oxide; Hexamethylphosphorous triamide; In dichloromethane;

DOI:10.1016/0008-6215(90)80018-X

Reference yield:

Acetic acid (3aS,4R,6S,7R,7aS)-4-acetoxymethyl-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-hydroxy-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester (130564-24-8) → O-(2,6-Di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose (126660-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / CBr₄, (Me₂N)3P, TMSOTf / CH₂Cl₂ / 16 h / 25 °C

2: 75 percent / Bu₄NBr, Et₃N / CH₂Cl₂ / 16 h / 60 °C

With carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; triethylamine; Hexamethylphosphorous triamide; In dichloromethane;

DOI:10.1016/0008-6215(90)80018-X

upstream raw materials:

O-(2,6-Di-O-acetyl-3,4-di-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl bromide

benzyl alcohol

Acetic acid (3aS,4R,6S,7R,7aS)-4-acetoxymethyl-6-((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-hydroxy-tetrahydro-pyran-3-yloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

Allyl O-(2,6-di-O-acetyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

benzyl 3,6-di-O-benzyl-4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside

Benzyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-O-acetyl-3,6-di-O-benzyl-β-D-glucopyranoside

Benzyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2-O-pivaloyl-3,6-di-O-benzyl-β-D-glucopyranoside

O-(2,6-Di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose