6340-57-4

Upstream product

• 67-56-1 methanol 
• 108-24-7 acetic anhydride 
• 67298-15-1 dapiramicin A 
• 7404-26-4 methyl 6-bromo-6-deoxy-β-D-glucopyranoside 
• 122204-71-1 methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-β-D-glucopyranoside 
• 19204-80-9 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-thioacetyl-β-D-glucopyranoside 
• 50692-55-2 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-mannopyranoside 
• 40984-39-2 methyl 2-O-acetyl-3,4,6-trideoxy-α-DL-erythro-hex-3-enopyranoside 
• 15562-20-6 methyl 3,4,6-trideoxy-α-DL-threo-hex-3-enopyranoside 
• 40984-39-2 methyl 2-O-acetyl-3,4,6-trideoxy-α-DL-threo-hex-3-enopyranoside 
• 109718-81-2 methyl 6-deoxy-α-L-talopyranoside 
• 42214-01-7 methyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 14133-63-2 methyl 6-deoxy-2,3-O-isopropylidene-α-L-talopyranoside 
• 42214-02-8 methyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-ulose 

Downstream Products

• 1128-40-1 methyl-6-desoxy-β-D-glucopyranoside 
• 73174-45-5 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran 

Relevant academic research and scientific papers

A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light to Synthesize Deoxyglycosides

We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2-5 min at room temperature, followed by de

Total synthesis of jadomycins B, S, T, and ILEVS1080

Sweetening up jadomycin A: The first total synthesis of jadomycins B, S, T, and ILEVS1080 has been achieved, featuring construction of the unique 8H-benz[b]oxazolo[3,3-f]phenanthridine skeleton by biomimetic condensation of a quinone aldehyde with amino acid sodium salts and elaboration of the glycosides by Mitsunobu condensation (see figure). Copyright

Synthesis of L-altrose and some derivatives

A convenient approach to the chemical synthesis of L-altrose (1) and its 6-deoxy derivative 2 has been developed by starting from D-galactose (9) and D-fucose (10), respectively. The 5-epimerization by a Mitsunobu inversion of the open-chain D-hexoses was the key step for these routes. Furthermore, the conversion of 2 into peracetylated TDP-6-deoxy-α-L-altrose (3a) was achieved by the cycloSal approach. However, the final deacetylation led to an unexpected side-reaction resulting in the previously unknown 6-deoxy-α-L-altropyranose 1,3-cyclophosphate (4).

A nonself sugar mimic of the HIV glycan shield shows enhanced antigenicity

Antibody 2G12 uniquely neutralizes a broad range of HIV-1 isolates by binding the high-mannose glycans on the HIV-1 surface glycoprotein, gp120. Antigens that resemble these natural epitopes of 2G12 would be highly desirable components for an HIV-1 vaccine. However, host-produced (self)-carbohydrate motifs have been unsuccessful so far at eliciting 2G12-like antibodies that cross-react with gp120. Based on the surprising observation that 2G12 binds nonproteinaceous monosaccharide D-fructose with higher affinity than D-mannose, we show here that a designed set of nonself, synthetic monosaccharides are potent antigens. When introduced to the terminus of the D1 arm of protein glycans recognized by 2G12, their antigenicity is significantly enhanced. Logical variation of these unnatural sugars pinpointed key modifications, and the molecular basis of this increased antigenicity was elucidated using high-resolution crystallographic analyses. Virus-like particle protein conjugates containing such nonself glycans are bound more tightly by 2G12. As immunogens they elicit higher titers of antibodies than those immunogenic conjugates containing the self D1 glycan motif. These antibodies generated from nonself immunogens also cross-react with this self motif, which is found in the glycan shield, when it is presented in a range of different conjugates and glycans. However, these antibodies did not bind this glycan motif when present on gp120.

SYNTHESIS OF METHYL 2,6-DIDEOXY-β-D-ARABINO-, 3,6-DIDEOXY-β-D-RIBO-, AND 4,6-DIDEOXY-β-D-XYLO-HEXOPYRANOSIDES

A convenient method is proposed for the synthesis of methyl 1,6-dideoxy-β-D-arabino-, 3,6-dideoxy-β-D-ribo-, and 4,6-dideoxy-β-D-xylo-hexopyranosides by the partial deoxygenation of methyl β-D-quinovopyranoside followed by liquid chromatography of the dideoxysugars.

OXYAMINATION OF UNSATURATED SUGAR DERIVATIVES. PART III. CIS-ADDITION OF β-TOLUENESULFONAMIDO AND HYDROXYL GROUPS TO THE DOUBLE BOND OF METHYL 3,4-DIDEOXY-α-DL-THREO- AND ERYTHRO-HEX-3-ENOPYRANOSIDES

Vicinal oxyamination of fifteen derivatives of methyl 3,4-dideoxy-α-DL-threo- and erythro-hex-3-enopyranosides with chloramine-T--osmium tetroxide (Sharpless reagent) was investigated.Under the conditions employed several methyl 3- and 4-deoxy-3- and 4-p-toluenesulfonamido-α-DL-hexopyranosides of altro, allo and galacto configuration, as well as their 6-amino-6-deoxy, and 6-deoxy analogs have been prepared.The oxyamination reaction was completely supressed if an allylic acyloxy group was present in the substrate; instead, dihydroxylated products, i.e. methyl hexopyranosides have been formed.

A CONVENIENT AND GENERAL SYNTHESIS OF 5-VINYLHEXOFURANOSIDES FROM 6-HALO-DEOXYPYRANOSIDES

The synthesis of five different 5,6-dideoxyhex-5-enofuranosides (5,7,9 and 11) proceeds in 30-60percent overall yield in two steps from commercially available 1-O-methyl pyranosides by reductive β-elimination of the intermediate 6-bromo-6-deoxypyranosides.