70287-09-1

Basic information

• Product Name: (2S,3S,4R)-2-(benzylamino)octadecane-1,3,4-triol
• Synonyms: (2S,3S,4R)-2-(benzylamino)octadecane-1,3,4-triol
• CAS NO: 70287-09-1
• Molecular Weight: 407.637
• Mol File: 70287-09-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3S,4R)-2-(benzylamino)octadecane-1,3,4-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4R)-2-(benzylamino)octadecane-1,3,4-triol(70287-09-1)
• EPA Substance Registry System: (2S,3S,4R)-2-(benzylamino)octadecane-1,3,4-triol(70287-09-1)

Safety Data

• Hazardous Substances Data: 70287-09-1(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 554-62-1 D-ribo-phytosphingosine 

Downstream Products

• 800407-55-0 (2S,3S,4R)-diisopropyl 3-(N-benzylamino)-3-(2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)propylphosphonate 
• 800407-54-9 (S)-3-Benzyl-4-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-[1,2,3]oxathiazolidine 2,2-dioxide 
• 1053251-92-5 (S)-3-Benzyl-4-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-[1,2,3]oxathiazolidine 2-oxide 
• 800407-53-8 (2S,3S,4R)-2-(N-benzylamino)-2-(2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)ethanol 
• 800407-51-6 (2S,3S,4R)-2-(N-benzylamino)-1-(tert-butyldimethylsilanyloxy)octadecane-3,4-diol 
• 554-62-1 D-ribo-phytosphingosine 

Relevant articles and documents

An efficient preparation of isosteric phosphonate analogues of sphingolipids by opening of oxirane and cyclic sulfamidate intermediates with α-lithiated alkylphosphonic esters

D-erythro-(2S,3R,4E)-Sphingosine-1-phosphonate (1), the isosteric phosphonate analogue of naturally occurring sphingosine 1-phosphate (1a), and D-ribo-phytosphingosine 1-phosphonate (2), the isosteric phosphonate analogue of D-ribo-phytosphingosine- 1-phosphate (2a), were synthesized starting with methyl 2,3-O-isopropylidene-D-glycerate (4) and D-ribo-phytosphingosine (3), respectively. Oxirane 12 was formed in eight steps from 4, and cyclic sulfamidate 22 was formed in five steps from 3. The phosphonate group was introduced via regioselective ring-opening reactions of oxirane 12 and cyclic sulfamidate 22 with lithium dialkyl methylphosphonate, affording 13 and 23, respectively. The synthesis of 1 was completed by SN2 displacement of chloromesylate intermediate 14b with azide ion, followed by conversion of the resulting azido group to a NHBoc group and deprotection. The synthesis of 2 was completed by cleavage of the acetal, N-benzyl, and alkyl phosphonate ester groups.