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

Base Information

• Chemical Name: dibenzyl (3aR,4S,5S,7R,7aS)-4-allyl-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate
• CAS No.: 1267385-40-9
• Molecular Formula: C₃₁H₃₈N₂O₇
• Molecular Weight: 550.652
• Mol file: 1267385-40-9.mol

Synonyms:

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

There total 7 articles about dibenzyl (3aR,4S,5S,7R,7aS)-4-allyl-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:

dibenzyl (3aS,4R,5S,7R,7aS)-4-oxohexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate (1198767-80-4) + allylmagnesium bromide (1730-25-2) → dibenzyl (3aR,4S,5S,7R,7aS)-4-allyl-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate (1267385-40-9) + dibenzyl (3aR,4R,5S,7R,7aS)-4-allyl-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

Guidance literature:

With chloro-trimethyl-silane; In tetrahydrofuran; at -78 - 25 ℃; for 4h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/cbic.201000591

Reference yield:

neomycin B x sulfate → dibenzyl (3aR,4S,5S,7R,7aS)-4-allyl-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate (1267385-40-9) + dibenzyl (3aR,4R,5S,7R,7aS)-4-allyl-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

Guidance literature:

Multi-step reaction with 6 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

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 50 °C / Inert atmosphere

6.1: chloro-trimethyl-silane / tetrahydrofuran / 4 h / -78 - 25 °C / Inert atmosphere

With hydrogenchloride; sodium periodate; chloro-trimethyl-silane; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 5.1: Dess-Martin oxidation;

DOI:10.1002/cbic.201000591

Reference yield:

dibenzyl (3aS,4R,5S,7R,7aS)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate (82509-76-0) → dibenzyl (3aR,4S,5S,7R,7aS)-4-allyl-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate (1267385-40-9) + dibenzyl (3aR,4R,5S,7R,7aS)-4-allyl-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 50 °C / Inert atmosphere

2: chloro-trimethyl-silane / tetrahydrofuran / 4 h / -78 - 25 °C / Inert atmosphere

With chloro-trimethyl-silane; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1: Dess-Martin oxidation;

DOI:10.1002/cbic.201000591

upstream raw materials:

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

allylmagnesium bromide

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

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