153547-53-6

Upstream product

• 136883-91-5 (2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 

Downstream Products

• 327986-26-5 3,4,6-tri-O-benzyl-2-tert-butyldimethylsilyloxymethyl-D-glucal 
• 876660-22-9 3,4-di(benzyloxy)-2-benzyloxymethylperhydro-α-cyclopropa[b]pyran-4-ylmethanol 
• 876660-21-8 3,4-di(benzyloxy)-2-benzyloxymethylperhydro-β-cyclopropa[b]pyran-4-ylmethanol 
• 1003194-59-9 C₃₁H₃₂O₅ 
• 850220-29-0 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-2-ulose 
• 850220-31-4 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-D-fructofuranose 
• 14233-64-8 tri-O-benzyl-D-arabinolactone 
• 1369811-33-5 N-(3,4,6-tri-O-benzyl-2-deoxy-2-C-methylene-β-D-arabino-hexopyranosyl)trichloroacetamide 
• 1161011-46-6 N-(3,4,6-tri-O-benzyl-2-deoxy-2-C-methylene-α-D-arabino-hexopyranosyl)trichloroacetamide 
• 153082-00-9 methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-(methylene)-α-D-arabinohexopyranoside 
• 1207741-72-7 (2S,4R,5S,6R)-2-(allyloxy)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-methylenetetrahydro-2H-pyran 
• 1207741-66-9 6-O-(3,4,6-tri-O-benzyl-2-deoxy-2-C-methylene-D-arabinohexopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 194083-84-6 3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-C-methylene-D-arabinohexopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Relevant academic research and scientific papers

Mitsunobu Reaction of 1,5-Anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-hex-1-enitols and 1,5-Anhydro-2-deoxy-4,6-O-protected-hex-1-enitols. A Novel Method for the Synthesis of 2-C-Methylene Glycosides and an Useful Alternative to Ferrier Rearrangeme

A simple and convenient method for the synthesis of aryl-3,4,6-tri-O-benzyl-2-deoxy-2-methylene-hexopyranosides 5, 6 and 7, glycosides which are not accessible by the conventional Ferrier rearrangement, has been described based on the Mitsunobu reaction o

Synthesis of dihydroxymethyl dihydroxypyrrolidines and steviamine analogues from C-2 formyl glycals

Synthesis of dihydroxymethyl dihydroxypyrrolidines from C-2 formyl d-glycals has been described via a common dicarbonyl intermediate. The hence obtained pyrrolidines have been further utilized for the synthesis of some steviamine analogues. The newly synthesized molecules have been evaluated for glycosidase inhibition against 6 commercially available enzymes and found to be active in the micromolar range, where one of the steviamine analogues showed good and selective inhibition of β-mannosidase (Helix pomatia).

Synthesis of C-2 methylene glycosides from C-2 propargyloxymethyl glycals exploiting the alkynophilicity of AuCl3

C-2 Methylene glycosides were synthesized from C-2 propargyloxymethyl glycals in a stereoselective manner using a catalytic quantity of AuCl3. The Au-catalyzed reaction was explored using various aglycones. The current protocol enables the prep

Radical reaction opening of glucosyl 1,2-cyclopropane derivatives: Synthesis of α and β C-glycosides and oxepane derivatives

α and β C-glycosides and oxepane derivatives are prepared by radical reaction opening of glucosyl 1,2-cyclopropane derivatives. Structures have been confirmed by NOE studies of NMR, FABMS and C-H analysis.

Stereoselective synthesis of a ketohexofuranose from an aldohexopyranose by a [6+1-1] strategy

Ozonolysis of 2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D- arabino-hex-1-enitol gave 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino- hex-2-ulose (5). Subsequent hydrolysis and acetylation of 5 provided 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-D

The particular sensitivity of silyl ethers of D-glucal toward two Vilsmeier - Haack reagents POCl3·DMF and (CF3SO2)2O·DMF. Their unique and selective conversion to the corresponding C(6)-O-formates

The two electrophilic Vilsmeier - Haack reagents POCl3·DMF 2 or (CF3SO2)2O·DMF 3 mediate the one-step and selective conversion of O-triethylsilyl (O-TES), O-tert-butyldimethylsilyl (O-TBDMS), O-tert-butyldiphenylsilyl (O-TBDPS), and O-triisopropylsilyl (O-TIPS) ethers of D-glucal to the corresponding C(6)-O-formates.

A New Ferrier System: 2-C-Acetoxymethylglycals. A Convenient Entry to 2-C-Methylene Glycosides

Synthesis of tri-O-benzyl-2-C-acetoxymethylglycals and subsequent Ferrier rearrangement to give 2-C-methylene glycosides is described.