Acetic acid (4aR,6S,7S,8S,8aR)-7-acetoxy-2-phenyl-6-((1S,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enylamino)-hexahydro-benzo[1,3]dioxin-8-yl ester

Base Information

• Chemical Name: Acetic acid (4aR,6S,7S,8S,8aR)-7-acetoxy-2-phenyl-6-((1S,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enylamino)-hexahydro-benzo[1,3]dioxin-8-yl ester
• CAS No.: 102131-09-9
• Molecular Formula: C₃₃H₄₁NO₁₄
• Molecular Weight: 675.687
• Mol file: 102131-09-9.mol

Synonyms:

Chemical Property of Acetic acid (4aR,6S,7S,8S,8aR)-7-acetoxy-2-phenyl-6-((1S,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enylamino)-hexahydro-benzo[1,3]dioxin-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (4aR,6S,7S,8S,8aR)-7-acetoxy-2-phenyl-6-((1S,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enylamino)-hexahydro-benzo[1,3]dioxin-8-yl ester

There total 3 articles about Acetic acid (4aR,6S,7S,8S,8aR)-7-acetoxy-2-phenyl-6-((1S,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enylamino)-hexahydro-benzo[1,3]dioxin-8-yl ester 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: 76.0%

C21H29NO8 (102069-51-2) + acetic anhydride (108-24-7) → 4,7-O-benzylidenevalidoxylamine A hexa-O-acetate (86733-60-0,102131-09-9)

Guidance literature:

With pyridine;

DOI:10.1002/anie.200905096

Reference yield: 42.0%

benzaldehyde dimethyl acetal (1125-88-8) + (+)-validoxylamine A (38665-10-0) + acetic anhydride (108-24-7) → Acetic acid (4aR,6S,7S,8S,8aR)-7-acetoxy-2-phenyl-6-((1S,4R,5S,6S)-4,5,6-triacetoxy-3-acetoxymethyl-cyclohex-2-enylamino)-hexahydro-benzo[1,3]dioxin-8-yl ester (86733-60-0,102131-09-9) + Acetic acid (4aR,6S,7S,8S,8aR)-7-acetoxy-6-((6S,7S,8S,8aR)-7,8-diacetoxy-2-phenyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-6-ylamino)-2-phenyl-hexahydro-benzo[1,3]dioxin-8-yl ester

Guidance literature:

With toluene-4-sulfonic acid; Yield given. Multistep reaction; 1.) DMF, 60 deg C, 6 h; 2.) pyridine, room temp., overnight;

DOI:10.1246/cl.1983.921

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) + (+)-validoxylamine A (38665-10-0) + acetic anhydride (108-24-7) → validoxylamine A octa-O-acetate (79527-24-5,79549-81-8,82309-78-2,82309-81-7,84622-06-0,84622-07-1,91464-89-0) + 4,7-O-benzylidenevalidoxylamine A hexa-O-acetate (86733-60-0,102131-09-9) + 4,7:4',7'-di-O-benzylidenevalidoxylamine A tetra-O-acetate

Guidance literature:

With pyridine; toluene-4-sulfonic acid; Yield given. Multistep reaction. Yields of byproduct given; 1)DMF, 60 deg C, 15-20 Hgmm, 6 h, 2) room temp., overnight;

upstream raw materials:

benzaldehyde dimethyl acetal

(+)-validoxylamine A

acetic anhydride

C₂₁H₂₉NO₈

Downstream raw materials:

7,2'',3'',4'',6''-penta-O-acetyl-2,3,4',5',6',7'-hexa-O-benzylvalidamycin A

7-O-acetyl-2,3,4',5',6',7'-hexa-O-benzylvalidoxylamine A

2,3,4',5',6',7'-hexa-O-benzylvalidoxylamine A

(4aR,6S,7S,8S,8aR)-7,8-bis(benzyloxy)-2-phenyl-N-((1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)cyclohex-2-en-1-yl)hexahydro-4H-benzo[d][1,3]dioxin-6-amine