1235555-29-9

Basic information

• Product Name: methyl (4-methylphenyl 5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate
• Synonyms: methyl (4-methylphenyl 5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate
• CAS NO: 1235555-29-9
• Molecular Weight: 539.56
• Mol File: 1235555-29-9.mol

Chemical Properties

• CAS DataBase Reference: methyl (4-methylphenyl 5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (4-methylphenyl 5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate(1235555-29-9)
• EPA Substance Registry System: methyl (4-methylphenyl 5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate(1235555-29-9)

Safety Data

• Hazardous Substances Data: 1235555-29-9(Hazardous Substances Data)

Upstream product

• 1235555-31-3 methyl (4-methylphenyl 5-amino-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate 
• 108-24-7 acetic anhydride 
• 6931-68-6 methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 
• 20298-35-5 N-acetylneuraminic acid methyl ester 
• 1071226-27-1 methyl (2-p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α/β-D-galacto-2-thio-nonulopyranosid)onate 
• 106-45-6 para-thiocresol 

Downstream Products

• 1235555-40-4 methyl (5-amino-7,8,9-tri-O-acetyl-5,4-N,O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate-(2->6)-(methyl 2,3,4-tri-O-benzoyl-α-D-galactopyranoside) 
• 1235555-42-6 6-trifluoroacetamidohexyl O-[methyl (5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate]-(2->3)-O-(2,6-di-O-benzyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 1235555-39-1 methyl (5-amino-7,8,9-tri-O-acetyl-5,4-N,O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate-(2->6)-(methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside) 
• 1590365-50-6 methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate 
• 1590365-52-8 methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside) onate 
• 1590365-43-7 C₂₃H₃₃NO₁₂ 
• 1590365-44-8 C₂₃H₃₃NO₁₂ 
• 1590365-46-0 C₃₈H₄₇NO₁₇ 
• 1590365-47-1 C₃₈H₄₇NO₁₇ 
• 1246533-58-3 C₂₆H₃₁NO₁₂S 
• 1487451-89-7 C₂₇H₄₁NO₁₄S 
• 1453169-48-6 (5-N-benzyloxyacetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside 
• 381716-71-8 (5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosyl)onate-(2→3)-p-toluyl-1-thio-β-D-galactopyranoside 
• 1453169-44-2 methyl (5-tert-butyloxycabonyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 

Relevant articles and documents

Donor-Reactivity-Controlled Sialylation Reactions

Although tremendous efforts have been made for the efficient preparation of sialosides, controlling the stereochemical outcome of sialylation reaction still remains one of the most challenging tasks due to the unique chemical structure of sialic acid. We developed a new strategy to statistically analyze the stereoselectivity of sialylation reactions on six types of p-tolyl thiosialosides in NIS/TfOH system using Relative Reactivity Value (RRV) as the indicator. Analysis of the reaction mechanism showed the formation of the relatively stable glycosyl bromide and glycosyl chloride intermediates from halide- and triflate-containing promotors in the absence of an acceptor. We found that the α/β-stereoselectivity, yields, and intermediate changes were associated with their donor reactivity. These findings enable to tailor the most suitable building blocks for stereo-controlled sialylation reactions.

Comparative studies on the O-sialylation with four different α/β-oriented (N-acetyl)-5-N,4-O-carbonyl-protected p-toluenethiosialosides as donors

Four types of 5-N,4-O-carbonyl-protected p-toluenethiosialosides were synthesized and their couplings with different acceptors were thoroughly investigated. The results indicate that the sialyl donor structure, the amount of glycosyl acceptor, and the detailed promotion conditions have great influence on the sialylation stereoselectivties and product yields. Under the (p-Tol)2SO/Tf2O activation conditions, the glycosylations with simple alcohols provided declined α-selectivities and higher yields with increasing the amounts of acceptors from 1.1 equiv to 2.0 equiv. However, the outcome of same sialylation was independent of the relative amounts of sugar alcohol acceptors. With NIS/TfOH as promoter, the α-selectivities of the sialylations were significantly improved compared with the cases activated by (p-Tol)2SO/Tf2O. In general, the difference in configuration of N-acetylated sialyl donors (D2 and D4) has little effect on the sialylation yield and stereoselectivity. In contrast, the N-deacetylated α/β sialyl donors (D1 and D3) show complex sialylation profiles with different acceptors.

5- N,4- O -carbonyl-7,8,9-tri- O -chloroacetyl-protected sialyl donor for the stereoselective synthesis of α-(2→9)-tetrasialic acid

(Figure presented) An efficient stereoselective synthesis of α-(2→9)-tetrasialic acid was achieved using tri-O-chloroacetyl- derivatized sialyl donor and a triol sialyl acceptor. Both the acceptor and the donor were also protected with a cyclic 5-N-4-O-carbonyl protecting group. The donor is highly reactive and enabled α-selective sialylation with various primary, secondary, and tertiary acceptors under in situ activation conditions (NIS/TfOH, -78 °C, acetonitrile/dichloromethane). The trans-fused oxazolidinone ring and O-chloroacetyl protecting groups were easily removed under mild reaction conditions to provide the fully deprotected α(2→9)-tetrasialic acid.