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

Base Information

• Chemical Name: 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
• CAS No.: 123170-24-1
• Molecular Formula: C₅₂H₅₈O₁₂
• Molecular Weight: 875.025
• Mol file: 123170-24-1.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 5 articles about 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 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:

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-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose (123170-24-1)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 4.05 g / 0.1N NaOMe / methanol / 5 h / 20 °C

4: 1) NaH / 1) DMF, 0 deg C, 1h 2) 16h, 20 deg C

With carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; sodium methylate; sodium hydride; triethylamine; Hexamethylphosphorous triamide; In methanol; dichloromethane;

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

Reference yield:

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) → 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 (123170-24-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / Bu₄NBr, Et₃N / CH₂Cl₂ / 16 h / 60 °C

2: 4.05 g / 0.1N NaOMe / methanol / 5 h / 20 °C

3: 1) NaH / 1) DMF, 0 deg C, 1h 2) 16h, 20 deg C

With tetrabutylammomium bromide; sodium methylate; sodium hydride; triethylamine; In methanol; dichloromethane;

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-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose (123170-24-1)

Guidance literature:

Multi-step reaction with 5 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

4: 4.05 g / 0.1N NaOMe / methanol / 5 h / 20 °C

5: 1) NaH / 1) DMF, 0 deg C, 1h 2) 16h, 20 deg C

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

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

upstream raw materials:

benzyl bromide

(3aR,5R,6S,7S,7aR)-2-Benzyloxy-6-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-5-hydroxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-ol

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

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

Downstream raw materials:

benzyl O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-O-pivaloyl-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

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

2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-2,4-bis-benzyloxy-5-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester