(3aS,4S,6R,7R,7aS)-7-(4-Bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Base Information

• Chemical Name: (3aS,4S,6R,7R,7aS)-7-(4-Bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran
• CAS No.: 84562-00-5
• Molecular Formula: C₂₄H₂₈Br₂O₆
• Molecular Weight: 572.291
• Mol file: 84562-00-5.mol

Synonyms:

Chemical Property of (3aS,4S,6R,7R,7aS)-7-(4-Bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4S,6R,7R,7aS)-7-(4-Bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

There total 3 articles about (3aS,4S,6R,7R,7aS)-7-(4-Bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 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:

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) → (3aS,4S,6R,7R,7aS)-7-(4-Bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (84562-00-5)

Guidance literature:

Multi-step reaction with 3 steps

1: p-toluenesulfonic acid / acetone / 5 h / Ambient temperature

2: water / acetone / Ambient temperature

3: potassium hydroxide / toluene / 2.5 h / Heating

With potassium hydroxide; water; toluene-4-sulfonic acid; In acetone; toluene;

DOI:10.1016/0008-6215(83)88274-3

Reference yield:

methyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside (13035-60-4,50705-56-1,75100-00-4,89387-76-8,118542-52-2,118542-53-3,143996-47-8,143996-48-9) → (3aS,4S,6R,7R,7aS)-7-(4-Bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (84562-00-5)

Guidance literature:

Multi-step reaction with 2 steps

1: water / acetone / Ambient temperature

2: potassium hydroxide / toluene / 2.5 h / Heating

With potassium hydroxide; water; In acetone; toluene;

DOI:10.1016/0008-6215(83)88274-3

Reference yield:

1-bromomethyl-4-bromobenzene (589-15-1) + methyl 2,3-O-isopropylidene-α-D-mannopyranoside (63167-69-1) → (3aS,4S,6R,7R,7aS)-7-(4-Bromo-benzyloxy)-6-(4-bromo-benzyloxymethyl)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran (84562-00-5)

Guidance literature:

With potassium hydroxide; In toluene; for 2.5h; Heating;

DOI:10.1016/0008-6215(83)88274-3

upstream raw materials:

1-bromomethyl-4-bromobenzene

methyl 2,3-O-isopropylidene-α-D-mannopyranoside

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

methyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside

Downstream raw materials:

methyl 2,4,6-tri-O-(p-bromobenzyl)-α-D-mannopyranoside