[(2S,3R,4S,11S,12R)-2-(acetyloxy)-7-amino-4,12-dihydroxy-10,13,15-trioxa-6,8-diazapentacyclo[7.4.1.1~3,12~.0~5,11~.0~5,14~]pentadec-7-en-2-yl]methyl acetate (non-preferred name)

Base Information

• Chemical Name: [(2S,3R,4S,11S,12R)-2-(acetyloxy)-7-amino-4,12-dihydroxy-10,13,15-trioxa-6,8-diazapentacyclo[7.4.1.1~3,12~.0~5,11~.0~5,14~]pentadec-7-en-2-yl]methyl acetate (non-preferred name)
• CAS No.: 13285-84-2
• Molecular Formula: C₁₅H₁₉N₃O₉
• Molecular Weight: 385.331

Synonyms:

Chemical Property of [(2S,3R,4S,11S,12R)-2-(acetyloxy)-7-amino-4,12-dihydroxy-10,13,15-trioxa-6,8-diazapentacyclo[7.4.1.1~3,12~.0~5,11~.0~5,14~]pentadec-7-en-2-yl]methyl acetate (non-preferred name)

Chemical Property:

• Vapor Pressure: 1.58E-17mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [(2S,3R,4S,11S,12R)-2-(acetyloxy)-7-amino-4,12-dihydroxy-10,13,15-trioxa-6,8-diazapentacyclo[7.4.1.1~3,12~.0~5,11~.0~5,14~]pentadec-7-en-2-yl]methyl acetate (non-preferred name)

There total 2 articles about [(2S,3R,4S,11S,12R)-2-(acetyloxy)-7-amino-4,12-dihydroxy-10,13,15-trioxa-6,8-diazapentacyclo[7.4.1.1~3,12~.0~5,11~.0~5,14~]pentadec-7-en-2-yl]methyl acetate (non-preferred name) 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:

(5S)-6,8t,10c-triacetoxy-8c-acetoxymethyl-(3at,7at,10bt)-3a,5,6,7a,8,9,10,10b-octahydro-1(3)H-5r,10ac-cyclo-6c,9c-epioxido-[1,4]dioxepino[5,6,7-de]quinazolin-2-ylamine; toluene-4-sulfonate (5141-89-9) → (5S)-8t-acetoxy-8c-acetoxymethyl-2-amino-(3at,7at,10bt)-3a,7a,8,9,10,10b-hexahydro-1(3)H-5r,10ac-cyclo-6c,9c-epioxido-[1,4]dioxepino[5,6,7-de]quinazoline-6,10c-diol (13285-84-2)

Guidance literature:

With hydroxylamine; In methanol; water;

DOI:10.1016/S0040-4020(01)98344-9

Reference yield:

acetic anhydride (108-24-7) + tetradotoxin (4368-28-9) → Diacetyl-anhydro-epitetrodotoxin (13285-84-2)

Guidance literature:

Multistep reaction; (i) TsOH, (ii) Py, (iii) aq. NH₃;

DOI:10.1016/0040-4039(64)83035-5

Reference yield:

(5S)-8t-acetoxy-8c-acetoxymethyl-2-amino-(3at,7at,10bt)-3a,7a,8,9,10,10b-hexahydro-1(3)H-5r,10ac-cyclo-6c,9c-epioxido-[1,4]dioxepino[5,6,7-de]quinazoline-6,10c-diol (13285-84-2) → 4,9-anhydrotetrodotoxin (13072-89-4)

Guidance literature:

With sulfuric acid;

DOI:10.1016/S0040-4020(01)98344-9

upstream raw materials:

(5S)-6,8t,10c-triacetoxy-8c-acetoxymethyl-(3at,7at,10bt)-3a,5,6,7a,8,9,10,10b-octahydro-1⁽³⁾H-5r,10ac-cyclo-6c,9c-epioxido-[1,4]dioxepino[5,6,7-de]quinazolin-2-ylamine; toluene-4-sulfonate

acetic anhydride

tetradotoxin

Downstream raw materials:

4,9-anhydrotetrodotoxin

Amino-desoxy-tetrodotoxin

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