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

Base Information

• Chemical Name: 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
• CAS No.: 123170-26-3
• Molecular Formula: C₅₅H₆₄O₁₂
• Molecular Weight: 917.106
• Mol file: 123170-26-3.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 15 articles about 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 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: 91.0%

pivaloyl chloride (3282-30-2) + (2S,3R,4R,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-ol (59263-36-4) → 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 (123170-26-3)

Guidance literature:

With dmap; In pyridine; at 80 ℃; for 18h;

DOI:10.1021/ja00204a028

Reference yield: 91.0%

benzyl 3,6-di-O-benzyl-4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside (59263-36-4) + pivaloyl chloride (3282-30-2) → 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 (123170-26-3)

Guidance literature:

With pyridine; dmap; at 80 ℃; for 15h;

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

Reference yield:

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) → 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 (123170-26-3)

Guidance literature:

Multi-step reaction with 3 steps

1: TMSOTf / CH₂Cl₂ / 1.5 h / 0 °C

2: 98 percent / NaOMe / methanol / 18 h / 60 °C

3: 91 percent / 4-DMAP / pyridine / 18 h / 80 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In pyridine; methanol; dichloromethane;

DOI:10.1021/ja00204a028

upstream 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

pivaloyl chloride

4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-D-glucopyranose

[(2R,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-yloxy]-dimethyl-(1,1,2-trimethyl-propyl)-silane

Downstream raw materials:

2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-2,4-bis-benzyloxy-5-((2S,3R,4S,5R,6R)-3-benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

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