6087-47-4

Upstream product

• 83-87-4 β-D-mannopyranose pentaacetate 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 4451-37-0 O³,O⁴,O⁶-triacetyl-galactopyranosyl chloride 
• 4451-37-0 O³,O⁴,O⁶-triacetyl-β-D-mannopyranosyl chloride 
• 18968-05-3 1,3,4,6-tetra-O-acetyl-β-D-mannopyranose 
• 36215-42-6 N-<3,4,6-tri-O-acetyl-β-D-glucopyranosyl>piperidine 
• 4451-37-0 3,4,6-tri-O-acetyl-β-D-glucopyranosyl chloride 
• 3867-86-5 Brigl's anhydride 
• 114284-13-8 (2R,3R,4S,5S,6R)-2-((2R,4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 136597-31-4 (2R,4aR,6R,7R,8R,8aS)-6-((2R,4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 136597-32-5 C₄₈H₅₆O₂₀ 
• 20147-90-4 (1R)-O³,O⁴,O⁶-triacetyl-O²-phenylcarbamoyl-1-piperidino-1,5-anhydro-D-glucitol 
• 126412-67-7 4-methoxycarbonyl-2-nitrobenzyl 2,3-di-O-acetyl-4,6-di-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 142386-73-0 C₂₇H₃₉NO₂₀ 
• 126412-68-8 4-carboxy-2-nitrobenzyl 4,6-di-O-α-D-glucopyranosyl-β-D-glucopyranoside 
• 126412-66-6 4-methoxycarbonyl-2-nitrobenzyl 2,3-di-O-acetyl-4-O-(2,4,6-tri-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

The reactions of β- and α-pyranose peracetates with PCl5, and utilization of the products to construct sarsasapogenin glycosides

The reactions of β- and α-pyranose peracetates with PCl5 gave products regioselectively chlorinated. The reactions of 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (5) and -β-D-galactopyranose (6) with PCl5 in CCl4 and that of methyl 2,3,4-tri-O-acetyl-β-D-glucuronatopyranose (7) with PCl5 in toluene gave 2-O-trichloroacetyl-β-D-pyranosyl chlorides 4, 12 and 14, respectively, as major products, and α-D-pyranosyl chlorides 11, 13 and 15, respectively, as minor products. On the other hand, the reactions of compounds 8 and 9 which were α-anomers of 5 and 6, respectively, with PCl5 gave as major products transformed acetyl groups at C-6 to -C(Cl) = CCl2 or -C(Cl)2-CCl3 group (16 and 17 from 8 and 18 from 9). The same reaction of 10, which was α-anomer of 7, gave α-chloride 15 as a major product. The glycosidation of sugar derivative 4 with sarsasapogenin 23 gave β-glycoside 24 (29.1%) and α-glycoside 25 (46.9%), and that of 12 with 23 gave β-glycoside 26 (24.0%) and α-glycoside 27 (40.8%). The improvement of the yields of β-glycosides 24 and 26 (66.9 and 62.1% for 24 and 26, respectively) in the glycosidations were accomplished by the employment of α-bromides 28 and 29 obtained from 4 and 6, respectively. The glycosidations of monoglycosides 30 and 31 obtained by the treatment 24 and 26, respectively, with ammonia-saturated ether with sugar acetate bromides 32 and 34 gave diglycoside derivatives 35 and 33, respectively.