DAUNOSAMINE HYDROCHLORIDE

Base Information

• Chemical Name: DAUNOSAMINE HYDROCHLORIDE
• CAS No.: 32385-06-1
• Molecular Formula: C₇H₁₅NO₃*ClH
• Molecular Weight: 197.662
• Mol file: 32385-06-1.mol

Synonyms:L-lyxo-Hexopyranoside,methyl 3-amino-2,3,6-trideoxy-, hydrochloride, a- (8CI); a-Methyl daunosaminide hydrochloride

Chemical Property of DAUNOSAMINE HYDROCHLORIDE

Chemical Property:

• Melting Point: 175-178°C dec.
• PSA: 64.71000
• LogP: 0.95820
• Storage Temp.: -20?C Freezer
• Solubility.: Methanol (Slightly), Water (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl a-L-daunosamide HCl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: DAUNOSAMINE HYDROCHLORIDE is used in the synthesis of (L)-Daunosamine and related amino sugars Methyl α-L-Daunosamine is used in the synthesis of (L)-Daunosamine and related amino sugars.

Technology Process of DAUNOSAMINE HYDROCHLORIDE

There total 29 articles about DAUNOSAMINE HYDROCHLORIDE 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: 88.0%

Methyl 2-iodo-3-amino-2,3,6-trideoxy-α-L-galactopyranoside hydrochloride (91366-56-2) → (2S,3S,4S)-4-amino-6-methoxy-2-methyltetrahydro-2H-pyran-3-ol hydrochloride (32385-06-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In methanol; benzene; for 5h; Heating;

DOI:10.1021/jo00195a013

Reference yield: 79.0%

methanol (67-56-1) + ((2S,3S,4S)-3,6-Dihydroxy-2-methyl-tetrahydro-pyran-4-yl)-carbamic acid tert-butyl ester → (2S,3S,4S)-4-amino-6-methoxy-2-methyltetrahydro-2H-pyran-3-ol hydrochloride (32385-06-1)

Guidance literature:

With hydrogenchloride; for 6h; Ambient temperature;

DOI:10.1021/jo970576f

Reference yield: 78.0%

methyl 3-amino-2,3,6-trideoxy-2-iodo-α-DL-altropyranoside hydrochloride (89128-75-6,91366-56-2,116429-71-1,116429-73-3) → (+/-)-Ristosamine methyl ether (32385-06-1,51869-34-2,54623-24-4,64938-62-1,72377-60-7,97413-80-4,115388-97-1,131528-45-5)

Guidance literature:

With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile); In methanol; toluene; at 80 ℃; for 8h;

upstream raw materials:

Methyl 2-iodo-3-amino-2,3,6-trideoxy-α-L-galactopyranoside hydrochloride

(3S,4S,5S)-3-[N-(tert-Butoxycarbonyl)amino]-5-hydroxyhexano-4-lactone

methanol

(3S,4S,5R)-3-(N-tert-butoxycarbonylamino)-5-dihydroxy-4-hexanolactone

Downstream raw materials:

Methyl 4-O-acetyl-3-acetamido-2,3,6-trideoxy-α-L-lyxopyranoside

Refernces

• 1、 Davies, Stephen G.,Smyth, G. Darren,Chippindale, Ann M.. "Syntheses of derivatives of L-daunosamine and its C-3 epimer employing as the key step the asymmetric conjugate addition of a homochiral lithium amide to tert-butyl (E,E)-hexa-2,4-dienoate". . p. 3089 - 3104. Retrieved 2007/10/03.
• 2、 Davies, Stephen G.,Smyth, G. Darren. "Asymmetric synthesis of methyl α-L-daunosaminide hydrochloride". . p. 1273 - 1274. Retrieved 2007/10/03.