(5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-3-(4-tolyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene

Base Information

• Chemical Name: (5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-3-(4-tolyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene
• CAS No.: 1197825-70-9
• Molecular Formula: C₂₃H₂₇NO₁₀
• Molecular Weight: 477.468
• Mol file: 1197825-70-9.mol

Synonyms:(5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-3-(4-tolyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene

Chemical Property of (5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-3-(4-tolyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-3-(4-tolyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene

There total 2 articles about (5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-3-(4-tolyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene 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: 95.0%

N-hydroxy-4-methylbenzenecarboximidoyl chloride (36288-37-6) + 3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-deoxy-D-gluco-hept-1-enitol (74310-44-4) → (5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-3-(4-tolyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene (1197825-70-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 17h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.bmc.2009.08.060

Reference yield:

p-methylbenzaldehyde oxime (3235-02-7,3717-15-5,3717-16-6,140461-26-3,140461-27-4) → (5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-3-(4-tolyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene (1197825-70-9)

Guidance literature:

Multi-step reaction with 2 steps

1: N-chloro-succinimide / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 20 °C / Inert atmosphere

With N-chloro-succinimide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2015.12.004

Reference yield: 93.0%

(5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-3-(4-tolyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene (1197825-70-9) → (5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(4-toluyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene-8,9,10-triol (1197825-76-5)

Guidance literature:

(5R,7R,8R,9S,10R)-8,9,10-tris(acetoxy)-7-[(acetoxy)methyl]-3-(4-tolyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene; With sodium methylate; In methanol; at 20 ℃; for 3h;

In methanol; pH=5;

DOI:10.1016/j.bmc.2009.08.060

upstream raw materials:

N-hydroxy-4-methylbenzenecarboximidoyl chloride

3,4,5,7-tetra-O-acetyl-2,6-anhydro-1-deoxy-D-gluco-hept-1-enitol

p-methylbenzaldehyde oxime

Downstream raw materials:

(5R,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(4-toluyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene-8,9,10-triol