108342-87-6

Basic information

• Product Name: 2,3,4,6-Tetra-O-pivaloyl-D-galactopyranosylamine
• Synonyms: 2,3,4,6-TETRA-O-PIVALOYL-BETA-D-GALACTOPYRANOSYLAMINE;2,3,4,6-tetra-O-pivaloyl-beta-D-galacto-pyranosyl;2,3,4,6-Tetra-O-Pivaloy-Beta-D-Galacto- Pyranosylamine;2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosylamine;.beta.-D-Galactopyranosylamine, 2,3,4,6-tetrakis(2,2-dimethylpropanoate);2,3,4,6-Tetra-O-pivaloyl-b-D-galactopyranosylamine;2,3,4,6-TETRA-O-PIVALOYL-D-GALACTOPYRANOSYLAMINE 99+%;2,3,4,6-TETRA-O-PIVALOYL-SS-D-GALACTOPYRANOSYLAMINE
• CAS NO: 108342-87-6
• Molecular Formula: C₂₆H₄₅NO₉
• Molecular Weight: 515.64
• Product Categories: Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis
• Mol File: 108342-87-6.mol

Chemical Properties

• Melting Point: 92-95 °C(lit.)
• Boiling Point: 528.692 °C at 760 mmHg
• Flash Point: 75.917 °C
• Appearance: /
• Density: 1.117 g/cm³
• Vapor Pressure: 2.9E-11mmHg at 25°C
• Refractive Index: 1.488
• PKA: 6.96±0.70(Predicted)
• CAS DataBase Reference: 2,3,4,6-Tetra-O-pivaloyl-D-galactopyranosylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-pivaloyl-D-galactopyranosylamine(108342-87-6)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-pivaloyl-D-galactopyranosylamine(108342-87-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 9
• Hazardous Substances Data: 108342-87-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4,6-Tetra-O-pivaloyl-D-galactopyranosylamine is used as a building block for the diastereoselective synthesis of adjacent P,C-stereogenic β-N-glycosidic linked α-aminophosphinates, which are important in the development of pharmaceutical compounds with potential therapeutic applications.

InChI:InChI=1/C26H45NO9/c1-23(2,3)19(28)32-13-14-15(34-20(29)24(4,5)6)16(35-21(30)25(7,8)9)17(18(27)33-14)36-22(31)26(10,11)12/h14-18H,13,27H2,1-12H3/t14-,15+,16+,17-,18-/m1/s1

Upstream product

• 606092-30-2 N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)acetamide 
• 131603-21-9 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl azide 
• 7296-64-2 β-D-galactopyranoside 
• 3282-30-2 pivaloyl chloride 
• 108342-85-4 1,2,3,4,6-penta-O-pivaloyl-β-D-galactopyranose 
• 606092-33-5 N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-p-anisamide 
• 108342-86-5 2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl azide 

Downstream Products

• 133578-30-0 N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-D-phenylglycinotrile 
• 133578-30-0 N-(2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranosyl)-D-phenylglycinotrile 
• 120255-29-0 C₃₄H₅₁NO₉ 
• 120255-30-3 C₃₃H₄₈FNO₉ 
• 120255-31-4 C₃₃H₄₈ClNO₉ 
• 1196447-20-7 4-nitro-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactosyl) benzylideneamine 
• 1196447-21-8 C₃₄H₅₁NO₁₀ 
• 1196447-19-4 C₃₃H₄₈BrNO₉ 
• 1380444-81-4 C₃₃H₄₈BrNO₉ 
• 198699-93-3 C₃₄H₄₈N₂O₉ 
• 1242070-71-8 C₃₄H₄₈F₃NO₉ 
• 1287297-32-8 (S)-5-((R)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(p-trifluoromethylphenyl)methyl)-5H-furan-2-one 
• 1287297-31-7 (S)-5-((R)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(p-methylphenyl)methyl)-5H-furan-2-one 
• 1287297-28-2 (S)-5-((R)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(4-fluorophenyl)methyl)-5H-furan-2-one 

Relevant articles and documents

N-glycosyl amides: Removal of the anomeric protecting group and conversion into glycosyl donors

Reactivity upon demand: Because of their stability towards acids, bases, and many oxidizing and reducing agents, N-glycosyl amides 1 (see scheme) can be used as anomerically protected carbohydrates. The amide function can be cleaved under mild conditions

Synthesis of a cisplatin derivative from lithocholic acid

A new steroidal-platinum(II) hybrid compound was synthesized using a simple and efficient methodology. The synthesis was performed by a convergent approach with cross metathesis (CM) as a key step. An olefin derived from lithocholic acid and a vinyl substituted ethylenediamine derived from L-serine were used as chiral building blocks, which were combined in the CM step. The most important advantage of this method was the utilization of L-serine as a cheap, stereoisomerically pure substrate. A steroid with a diamino system in the side chain was subjected to reaction with potassium tetrachloroplatinate to obtain the target platinum(II) complex. Attempts to synthesize similar diamine systems using the asymmetric Strecker reaction were unsuccessful.

Stereoselective synthesis of bromopiperidinones and their conversion to annulated heterocycles

N-Galactopyranosyl- and N-glucopyranosyl imines of aliphatic, aromatic and heteroaromatic aldehydes react with 1-methoxy-3-trimethylsilyloxy-1,3-butadiene in a domino Mannich-Michael reaction cascade to give 2-substituted 5,6-dehydro-piperidin-4-ones with high diastereoselectivity. Treatment of these cyclic enaminones with N-bromo-succinimide yields the corresponding 2-substituted 5-bromo-5,6-dehydropiperidinones which react with L-Selectride or methylcuprate to afford the saturated bromo-piperidinones with high diastereoselectivity. Condensation reactions of these products with thioamides afford thiazolopiperidines.

N-glycosyl amides as glycosyl donors in stereoselective glycosylation reactions

Due to their high stability, N-glycosyl amides have so far not been considered as glycosyl donors for glycosylation reactions. Two new procedures for the cleavage of the anomeric amide functionality under mild reaction conditions and further stereoselecti

Carbohydrates as Chiral Templates: Stereoselective Strecker Synthesis of D-α-Amino Nitriles and Acids Using O-Pivaloylated D-Galactosylamine as the Auxiliary

The asymmetric synthesis of N-galactosyl D-α-amino nitriles is accomplished by application of 2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosylamine (4) as the stereodifferentiating template in Strecker reactions.Aldimines 6 derived from 4 and aromatic or ali