3306-06-7

Usage

Uses

Used in Pharmaceutical Industry:
1S,2S-(+)-2-amino-1-phenylpropane-1,3-diol is used as a key intermediate in the synthetic preparation of aryl-substituted indazole derivatives. These derivatives act as modulators and inhibitors of protein kinases, which play a crucial role in the regulation of cell growth, proliferation, and angiogenesis. By targeting these kinases, the aryl-substituted indazole derivatives can potentially be employed in the treatment of tumor growth and other related conditions.

InChI:InChI=1/C9H13NO2/c10-8(6-11)9(12)7-4-2-1-3-5-7/h1-5,8-9,11-12H,6,10H2/t8-,9-/m0/s1

Upstream product

• 50-00-0 formaldehyd 
• 614-21-1 2-nitroacetophenone 
• 52239-32-4 1,3-Dihydroxy-2-Nitro-1-phenylpropane 
• 60317-41-1 ethyl 2-(hydroxyimino)-3-oxo-3-phenylpropanoate 
• 94860-72-7 3-hydroxy-1-phenyl-2-(2-phenylhydrazono)propan-1-one 
• 38114-29-3 (+/-)-methyl (βS)-β-hydroxy-1-phenylalaninate 
• 15917-28-9 (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester 
• 337512-10-4 3-oxo-3-(p-chlorophenyl)-2-phenylhydrazonopropanal 
• 60083-18-3 3-oxo-3-phenyl-2-(phenylhydrazono)propanal 
• 625-48-9 2-nitro-1-ethanol 
• 100-52-7 benzaldehyde 
• 42267-16-3 erythro-DL-β-phenylserine ethyl ester hydrochloride 
• 69-96-5 (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid 
• 15823-87-7 phenylglyoxal-2-(Z)-phenylhydrazone 

Downstream Products

• 106454-69-7 N-tert-butoxycarbonyl-D-Phenylalaninol 
• 1227059-91-7 C₁₁H₁₂F₃NO₃ 
• 53732-41-5 (+/-)-(2-methyl-5c-phenyl-4,5-dihydro-oxazol-4r-yl)-methanol 
• 25126-19-6 (1RS,2SR)-2-(2,2-dichloro-acetylamino)-1-phenyl-propane-1,3-diol 
• 102312-49-2 (2RS,3SR)-2-amino-3-chloro-3-phenyl-propan-1-ol 
• 3306-06-7 (+/-)-threo-2-amino-1-phenyl-1,3-propanediol 
• 3313-19-7 (1RS,2SR)-2-acetylamino-1-phenyl-propane-1,3-diol 
• 3509-75-9 (1RS,2SR)-1,3-diacetoxy-2-acetylamino-1-phenyl-propane 
• 115964-09-5 (1RS:2SR)-2-benzamino-3-benzoyloxy-1-phenyl-propanol-⁽¹⁾ 
• 3313-16-4 (1RS,2SR)-2-benzoylamino-1,3-bis-benzoyloxy-1-phenyl-propane 
• 60204-56-0 4a,6a-dimethyl-2t-phenyl-(2ar,4aξ,6aξ)-hexahydro-1,4-dioxa-6b-aza-cyclopenta[cd]pentalene 
• 94027-44-8 [(RS)-5-((SR)-hydroxy-phenyl-methyl)-2-oxo-morpholin-3-ylidene]-acetic acid ethyl ester 

Relevant academic research and scientific papers

Micro-reaction system and method for continuously preparing 2-amino-1,3-diol compounds

The invention belongs to the technical field of pharmaceutical engineering, and particularly relates to a micro-reaction system and method for continuously preparing 2-amino-1,3-diol compounds. The micro-reaction system comprises a micro-mixer and a micro-channel reactor which communicate with each other in sequence; the micro-mixer is used for mixing a solution of a raw material 2-nitro-1,3-diol compound with hydrogen; and the micro-channel reactor is used for continuous reaction of the mixture. The method comprises the following steps: packing a palladium catalyst in the microchannel reactor, dissolving a 2-nitro-1,3-diol compound in an organic solvent, conveying the dissolved 2-nitro-1,3-diol compound and hydrogen into the microchannel reactor at the same time, and carrying out a continuous catalytic hydrogenation reaction to obtain the corresponding 2-amino-1, 3-diol compound. According to the method, the reaction time is only several minutes, the yield of the product 2-amino-1,3-diol compound is larger than 99%, the technological process is continuous, the automation degree is high, the space time yield is high, operation is easy and convenient, the step of separating reaction liquid from a catalyst is not needed, cost is low, and the method is environmentally friendly, safe and easy for industrial production.

Oxidant controlled regio- and stereodivergent azidohydroxylation of alkenes via I2 catalysis

A novel, I2 catalyzed regio- and stereodivergent vicinal azidohydroxylation of alkenes leading to 1,2-azidoalcohols in high yields (up to 92%) and excellent dr (up to 98%) has been developed. This unprecedented transformation employs NaN3 and DMF as N- and O-nucleophiles respectively. The role of DMF as the O-source in the reaction has been unequivocally proven by 18O labelling studies.

PPMP as a ceramide catabolism inhibitor for cancer treatment

The present invention relates to a method of treating a hyperproliferative disorder comprising administering a ceramide generating retinoid comprising a retinoic acid derivative or a pharmaceutically acceptable salt thereof, and D-threo-PPMP as a ceramide degradation inhibitor or a pharmaceutically acceptable salt thereof, wherein the hyperproliferative disorder is a tumor; and wherein the ceramide generating retinoid is administered in an amount effective to produce necrosis, apoptosis or both in the tumor, and the ceramide degradation inhibitor is administered in an amount effective to increase the necrosis, apoptosis or both in the tumor over that expected to be produced by the sum of that produced by the ceramide generating retinoid and the ceramide degradation inhibitor when administered separately.

STEREOSELECTIVE SYNTHESIS OF (+/-)-threo-2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL

Addition of hypobromic acid to styrene afforded styrene bromohydrin (I) which was dehydrated to ω-bromostyrene (II).Prince reaction of II with aqueous formaldehyde gave 5-bromo-4-phenyl-1,3-dioxane (III).The bromine atom in III was replaced with amino group by treatment with methanolic ammonia at 150 deg C and 6 - 8 MPa and the obtained threo-5-amino-4-phenyl-1,3-dioxane (IVa) was hydrolyzed to give (+/-)-threo-2-amino-1-phenyl-1,3-propanediol (V).Suitably chosen method of nitration converted the free base IVa or its N-acetyl derivative IVb into 5-amino-4-(4-nitrophe nyl)-1,3-dioxane (VIa) or its N-acetyl derivative VIb which without isolation were hydrolyzed to threo-2-amino-1-(4-nitrophenyl)-1,3-propanediol (VII), isolated as hydrochloride.The liberated base was resolved into enantiomers and dichloroacetylated in the known manner to give D-(-)-threo-2-dichloroacetylamino-1-(4-nitrophenyl)-1,3-propanediol (chloramphenicol).

Resolution of Racemic Amines with 2-Methyl-2-phenylbutanedioic Acid

Five racemic amines were resolved in high chemical and optical yields using (S)-(+)-2-methyl-2-phenylbutanedioic acid as resolving reagent.The reagent can be recovered quantitatively and without any change in its optical purity. (R)-(-)-2-Methyl-2-phenylbutanedioic acid was also obtained.

Note on a Simple Synthesis of (+/-)-threo-2-Amino-1-phenyl-1,3-propanediole

A synthesis of the title compound starting from methyl trans-5-phenyl-2-oxazoline-4-carboxylate (3) is described.