81823-12-3

Upstream product

• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 100-39-0 benzyl bromide 
• 620-05-3 iodomethylbenzene 
• 3587-60-8 Benzyloxymethyl chloride 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 100-51-6 benzyl alcohol 
• 35781-78-3 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 100-44-7 benzyl chloride 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 118895-89-9 5-O-acetyl-3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 20194-18-7 sodium phenyl-methanolate 
• 53928-30-6 1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside 

Downstream Products

• 59541-28-5 3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranose-5-ulose 
• 115351-15-0 1,2-O-isopropylidene-3,6-di-O-benzyl-5-azido-5-deoxy-β-L-idofuranose 
• 81823-13-4 3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose (E) 5-p-tolylsulfonylhydrazone 
• 220204-88-6 (5S)-3,6-di-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 220204-91-1 (5R)-3,6-di-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 118895-89-9 5-O-acetyl-3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 115351-19-4 Trifluoro-methanesulfonic acid (R)-2-benzyloxy-1-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester 

Relevant academic research and scientific papers

An easy and versatile approach for the regioselective De-O-benzylation of protected sugars based on the I2/Et3SiH combined system

The use of cheap and easy to handle reagents, such as I2 and Et3SiH, at low temperature allows the regioselective removal of benzyl protecting groups from highly O-benzylated carbohydrates. The observed regioselectivity is dependent

A simple, mild, and regioselective method for the benzylation of carbohydrate derivatives promoted by silver carbonate

A simple, mild, and regioselective method has been developed for the selective benzylation and p-methoxybenzylation of carbohydrate derivatives in high yields using Ag2CO3 as the promoter. Benzylation of base-labile substrates, for w

Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)

The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereosel

Regioselective de-O-benzylation of monosaccharides

Poly-O-benzylated sugars are regioselectively debenzylated using CrCl2/LiI in moist EtOAc. A predictive, three-point coordination model is proposed.

Synthesis of peracetylated chacotriose

Steroidal glycoalkaloids of many Solanum species have recognized biological activities, especially those containing the glycosyl moiety α-L-rhamnopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 4)]-D-glucopyranose (chacotriose) whose peracetate is here synthe

Elongation of the pentose chain at the terminal carbon atom with Grignard C1 reagents. A study of the homologation reaction

Derivatives of four stereoisomeric pentodialdo-1,4-furanoses were reacted with four Grignard C1 reagents: methoxymethyl-, allyloxymethyl-, benzyloxymethyl, and dimethylphenylsilylmethyl-magnesium chlorides. Derivatives of the expected stereoisomeric hexoses were accompanied in some cases by C-4 inverted products. The results have been discussed in terms of α- and β-chelated transition states. It has been found that the RX (X=O,Si) grouping of the Grignard reagent strongly influences the stereochemical outcome of the elongation reaction.

Control of regioselectivity in reactions of dialkylstannylene acetals. Part I. A dramatic reversal of regioselectivity in mono-p-toluenesulfonation reactions

The regioselectivities of p-toluenesulfonation reactions of dialkylstannylene acetals obtained from a number of carbohydrate-derived terminal 1,2-diols in the absence of added nucleophiles have been explored as functions of the carbohydrate structure, the

A convenient preparation of 5-benzyl ethers of D-gluco- and D-manno-furanose derivatives

Keywords: Glucofuranose; Mannofuranose; Selective benzylation; Two-phase benzylation

Regioselective De-O-benzylation with Lewis Acids

Simple and highly regioselective de-O-benzylations of poly-O-benzylated monosaccharides and polyols with Lewis acids (SnCl4 and TiCl4) were developed.Spectral studies on intermediates complexes showed that three appropriately situated metal chelating functional groups were necessary for the selective de-O-benzylation.

Synthesis of the antibiotic 1,5-dideoxy-1,5-imino-D-glucitol; concomitant formation of the D-mannitol analogue

The easy accessible 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose was converted in six steps into 1,2-O-isopropylidene-3,6-di-O-benzyl-5-deoxy-5-azido-α-D-glucofuranose.The latter afforded, after acidolysis followed by hydrogenolysis, 1-deoxynojirimicine and a small quantity of 1-deoxymannonojirimicine.The antibiotic thus obtained had an inhibitory effect on the trimming of N-linked carbohydrates in IgM.