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
• Article Data: 6

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

Chemical Properties

White to off-white powder

Uses

2,3,4,6-Tetra-O-pivaloyl-D-galactopyranosylamine (CAS# 108342-87-6) is a useful building block used in the diastereoselective synthesis of adjacent P,C-stereogenic β-N-glycosidic linked α-aminophosphinates.

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

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

Downstream Products

• 112022-94-3 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((R)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 112022-94-3 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((S)-1-tert-butylcarbamoyl-2-phenyl-ethyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 112022-94-3 N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(R)-phenylalanine-N'-tert-butyl-amide 
• 112022-94-3 N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-phenylalanine-N'-tert-butyl-amide 
• 121841-86-9 4-fluoro-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)benzylideneamine 
• 112022-98-7 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-{[(S)-tert-butylcarbamoyl-(4-chloro-phenyl)-methyl]-formyl-amino}-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 112022-98-7 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-{[(R)-tert-butylcarbamoyl-(4-chloro-phenyl)-methyl]-formyl-amino}-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 119825-39-7 N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-p-chloro-phenylglycine-N'-tert-butyl-amide 
• 112022-98-7 N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(R)-p-chloro-phenylglycine-N'-tert-butyl-amide 
• 108365-46-4 4-chloro-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-D-phenylglycinotrile 
• 133646-16-9 4-chloro-N-(2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranosyl)-D-phenylglycinotrile 
• 112022-97-6 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((S)-tert-butylcarbamoyl-phenyl-methyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 112022-97-6 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((R)-tert-butylcarbamoyl-phenyl-methyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 119825-38-6 N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-phenylglycine-N'-tert-butyl-amide 

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

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.

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