[(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-(2-aminopropanoyl)sulfamate

Base Information

Chemical Name:[(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-(2-aminopropanoyl)sulfamate
CAS No.:91432-48-3
Molecular Formula:C₁₃H₁₈ClN₇O₇S
Molecular Weight:451.848
Hs Code.:
DSSTox Substance ID:DTXSID30919732
Wikidata:Q82892304
Mol file:91432-48-3.mol

Synonyms:ascamycin

Suppliers and Price of [(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-(2-aminopropanoyl)sulfamate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

American Custom Chemicals Corporation
ASCAMYCIN 95.00%
5MG
$ 497.12

Total 7 raw suppliers

Chemical Property of [(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-(2-aminopropanoyl)sulfamate

Chemical Property:

Boiling Point:°Cat760mmHg
Flash Point:°C
PSA：226.18000
Density:2.12g/cm³
LogP:0.15910
XLogP3:-2.4
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:6
Exact Mass:451.0676948
Heavy Atom Count:29
Complexity:712

Purity/Quality:

97% ^*data from raw suppliers

ASCAMYCIN 95.00% ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(C(=O)NS(=O)(=O)OCC1C(C(C(O1)N2C=NC3=C(N=C(N=C32)Cl)N)O)O)N
Isomeric SMILES:CC(C(=O)NS(=O)(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=C(N=C32)Cl)N)O)O)N

Technology Process of [(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-(2-aminopropanoyl)sulfamate

There total 5 articles about [(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-(2-aminopropanoyl)sulfamate 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%

: 110231-47-5
2-chloro-9-<2',3'-O-isopropylidene-5'-O-(N-t-butyloxycarbonyl-L-alanyl)sulfamoyl-β-D-ribofuranosyl>adenine

: 91432-48-3
ascamycin

Guidance literature:: With water; trifluoroacetic acid; for 2h; Ambient temperature;
DOI:10.1016/S0040-4020(01)89967-1

Reference yield: 79.0%

: 103251-78-1
N⁶-t-butyloxycarbonyl-2-chloro-9-<2',3'-O-isopropylidene-5'-O-(N-t-butyloxycarbonyl-L-alanyl)sulfamoyl-β-D-ribofuranosyl>adenine

: 91432-48-3
ascamycin

Guidance literature:: With trifluoroacetic acid; 0 deg C, 15 min; room temp., 1 h;
DOI:10.1271/bbb1961.52.1117

Reference yield:

: 24639-06-3
((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

: 91432-48-3
ascamycin

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) bis(tri-n-butyltin)oxide; 2.) sulfamoyl chloride / 1.) benzene, reflux; 2.) dioxane, 5 deg C - 20 deg C, 35 h

2: 85 percent / NaH / dimethylformamide; paraffin / 2 h / -20 - 0 °C

3: 86 percent / Cs₂CO₃ / dimethylformamide / 8 h / -20 - 20 °C

4: 79 percent / 90 percent aqu. trifluoroacetic acid / 0 deg C, 15 min; room temp., 1 h

With sulphamoyl chloride; sodium hydride; caesium carbonate; trifluoroacetic acid; bis(tri-n-butyltin)oxide; In N,N-dimethyl-formamide; paraffin;
DOI:10.1271/bbb1961.52.1117