(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

Base Information

• Chemical Name: (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
• CAS No.: 126660-01-3
• Molecular Formula: C₂₄H₃₄O₁₂
• Molecular Weight: 514.527
• Mol file: 126660-01-3.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 4 articles about (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 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:

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) → (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 (126660-01-3)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 5h;

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) → (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 (126660-01-3)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With tetrabutylammomium bromide; sodium methylate; triethylamine; In methanol; 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) → (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 (126660-01-3)

Guidance literature:

Multi-step reaction with 3 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

With carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; sodium methylate; triethylamine; Hexamethylphosphorous triamide; In methanol; 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)-3,6-di-O-acetyl-1,2-O-(1-benzyloxyethylidene)-α-D-glucopyranose

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

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