dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

Base Information

• Chemical Name: dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate
• CAS No.: 82509-76-0
• Molecular Formula: C₂₈H₃₄N₂O₇
• Molecular Weight: 510.587
• Mol file: 82509-76-0.mol

Synonyms:dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

Chemical Property of dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

There total 5 articles about dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate 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: 94.0%

1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-5,6-O-cyclohexylideneneamine (55728-75-1) → dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate (82509-76-0)

Guidance literature:

1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-5,6-O-cyclohexylideneneamine; With sodium periodate; In methanol; at 0 - 25 ℃; Inert atmosphere; Darkness;

With triethylamine; In methanol; at 40 ℃; for 13h; Inert atmosphere;

DOI:10.1002/cbic.201000591

Reference yield:

cycloxexanone dimethyl ketal (933-40-4) → dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate (82509-76-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 5 h / 50 °C / Inert atmosphere

1.2: 1 h / 50 °C

1.3: 20 °C

2.1: sodium periodate / methanol / 0 - 25 °C / Inert atmosphere; Darkness

2.2: 13 h / 40 °C / Inert atmosphere

With sodium periodate; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/cbic.201000591

Reference yield:

neomycin B x sulfate → dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate (82509-76-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride / methanol; water / 6 h / Reflux

2.1: sodium hydrogencarbonate / water / 0.33 h

2.2: 16 h / 0 - 25 °C

3.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 5 h / 50 °C / Inert atmosphere

3.2: 1 h / 50 °C

3.3: 20 °C

4.1: sodium periodate / methanol / 0 - 25 °C / Inert atmosphere; Darkness

4.2: 13 h / 40 °C / Inert atmosphere

With hydrogenchloride; sodium periodate; sodium hydrogencarbonate; toluene-4-sulfonic acid; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1002/cbic.201000591

upstream raw materials:

1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-5,6-O-cyclohexylideneneamine

cycloxexanone dimethyl ketal

N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine

neamine tetrahydrochloride

Downstream raw materials:

dibenzyl (3aS,4R,5S,7R,7aS)-4-oxohexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

dibenzyl (3aR,4S,5S,7R,7aS)-4-hydroxy-4-vinylhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

dibenzyl (3aR,4S,5S,7R,7aS)-4-allyl-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

dibenzyl (3aR,4S,5S,7R,7aS)-4-(but-3-enyl)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate