172223-07-3

Basic information

• Product Name: (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-yl)oxy)(tert-butyl)dimethylsilane
• Synonyms: (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-yl)oxy)(tert-butyl)dimethylsilane
• CAS NO: 172223-07-3
• Molecular Weight: 688.718
• Mol File: 172223-07-3.mol

Chemical Properties

• CAS DataBase Reference: (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-yl)oxy)(tert-butyl)dimethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-yl)oxy)(tert-butyl)dimethylsilane(172223-07-3)
• EPA Substance Registry System: (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-yl)oxy)(tert-butyl)dimethylsilane(172223-07-3)

Safety Data

• Hazardous Substances Data: 172223-07-3(Hazardous Substances Data)

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 294872-82-5 (2α,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-vinyltetrahydro-2H-pyran-3-ol 
• 908838-45-9 1-deoxy-1-α-ethenyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 160318-52-5 (2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(iodomethyl)tetrahydro-2H-pyran-3-ol 
• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 93125-77-0 (2R,3R,4R,5S)-1,3,4-tris(benzyloxy)hept-6-ene-2,5-diol 
• 93125-49-6 (((2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxytetrahydro-2H-pyran-2-yl)methyl)mercury(II) chloride 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 908838-46-0 1-deoxy-1-α-hydroxymethyl-2-O-(tert-butyldimethylsilyl)-3,4,5-tri-O-benzyl-D-glucose 

Downstream Products

• 172223-08-4 diethyl (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methyl)phosphonate 
• 172223-09-5 diethyl (((2S,3R,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-hydroxytetrahydro-2H-pyran-2-yl)methyl)phosphonate 
• 172223-10-8 diethyl (((2S,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-oxotetrahydro-2H-pyran-2-yl)methyl)phosphonate 
• 172223-11-9 diethyl (((2S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-(hydroxyimino)tetrahydro-2H-pyran-2-yl)methyl)phosphonate 
• 176590-52-6 diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate 
• 176515-25-6 C₃₄H₄₂NO₉P 

Relevant articles and documents

CARBOHYDRATE PHOSPHONATE DERIVATIVES AS MODULATORS OF GLYCOSYLATION

Compounds of Formula (I) are useful as modulators of glycosylation. Compounds of Formula (I) have the following structure: (I) and the definitions of the other variables are provided herein.

IMMUNOGENS FOR MENINGITIDIS-A VACCINES

An oligosaccharide useful for a Meningitidis A vaccine contains a first mannose unit having a spacer in the alpha configuration at C-1, which spacer is capable of conjugating to a protein, and which is connected to a second mannose unit through a 1,6-linkage which connects C-6 of the first unit to C-1 of the second unit, wherein the 1,6-linkage comprises a phosphonate. Related methods of making such compounds, analogous compounds, or intermediates thereof are also disclosed.

Synthesis of the C1-phosphonate analog of UDP-GlcNAc

We describe the first synthesis of the C1-phosphonate analog of UDP-GlcNAc, based on a new preparation of the corresponding glycosyl phosphonate. This C-glycosyl analog is shown to be a very weak inhibitor (Ki > 10 mM) of fungal chitin synthase

Stereoselective synthesis of the isosteric phosphono analogues of N-acetyl-α-D-glucosamine 1-phosphate and N-acetyl-α-D-mannosamine 1-phosphate

The isosteric phosphono analogues of N-acetyl-α-D-glucosamine 1-phosphate and N-acetyl-α-D-mannosamine 1-phosphate (1 and 2) are stereoselectively synthesized starting from 2,3,5-tri-O-benzyl-D-arabinose (3b). Reaction of 3b with divinylzinc stereoselectively affords the glucoenitol 4c, the mercuriocyclization and subsequent iododemercuriation of which stereoselectively afford the α-C-glucopyranosyl iodide 6b with a free hydroxyl group at C-2. Temporary protection of the hydroxyl group and treatment with triethyl phosphite converts 6b into the corresponding phosphonate 7b. The free hydroxyl group of 7b is then converted into an acetamido group by oximation, acetylation of the oxime, reduction, and subsequent acetylation. The reduction of the oxime with diborane stereoselectively affords the gluco isomer, whereas catalytic hydrogenation gives the manno isomer. Acetylation and deprotection afford the desired products 1 and 2.

First Synthesis of the Phosphono Analogue of N-Acetyl-α-D-mannosamine 1-Phosphate

Reaction of 2,3,5-tri-O-benzyl-D-arabinose with divinylzinc, and subsequent mercuriocyclisation and iodomercuriation stereoselectively affords the α-C-glucopyranosyl iodide 3 with a free hydroxy group at C-2; temporary protection of the free hydroxy group