82209-93-6

Upstream product

• 63166-73-4 Phyllanthoside 
• 109922-63-6 3-O-(chloroacetyl)-4-O-acetyl-6-deoxy-2-O-(2,4-bis-O-(chloroacetyl)-3-O-acetyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranose 
• 114828-01-2 Chloro-acetic acid (3R,4S,5R,6R)-2,5-diacetoxy-3-[(2S,3R,4S,5R,6R)-4-acetoxy-3,5-bis-(2-chloro-acetoxy)-6-methyl-tetrahydro-pyran-2-yloxy]-6-methyl-tetrahydro-pyran-4-yl ester 
• 114828-04-5 1-O-phyllanthocinoyl 3-O-(chloroacetyl)-4-O-acetyl-6-deoxy-2-O-(2,4-bis-O-(chloroacetyl)-3-O-acetyl-6-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside 

Downstream Products

• 62955-96-8 C₄₆H₅₈O₂₀ 

Relevant academic research and scientific papers

Phyllanthoside-Phyllanthostatin Synthetic Studies. 9. Total Syntheses of (-)-Phyllanthostatin 1, (+)-Phyllanthostatin 2, and (+)-Phyllanthostatin 3

Phyllanthostatins 1, 2, and 3 (2-4) have been synthesized for the first time. The unusual 1′→2β glycosidic linkages of the disaccharide moieties were constructed via anchimerically-assisted Koenigs-Knorr reactions. The novel β-glycosyl esters were then ge

The Total Synthesis of (-)-Phyllanthostatin-1

The first total synthesis of the important antitumor glycoside (-)-phyllanthostatin-1 (1) is described; the key steps include a regioselective Koenigs-Knorr reaction to establish the 1,2-O-linkage in disaccharide (6) and a stereoselective triphenylphosphine-di-isopropyl azodicarboxylate (TPP-DIAD) glycosidation of hemiacetal (12) with aglycone (15).

Phyllanthostatin 1-Phyllanthoside Orthoacid Rearrangement

Solvolysis of phyllanthoside (1b) in 1:9 ethanol-water (14 days at room temperature) consumed about 54percent of the starting glycoside and afforded the S3'-monoacetyl derivative 1f and phyllanthostatins 1 (1a) and 4 (1e) in 8-10percent yields accompanied by five related products of orthoacid rearrangement and/or deacetylation.Several additional minor transformation products were detected by HPLC analyses.When phyllathostatin 1 (1a) was subjected to the same solvolysis reaction for 21.5 h, approximately half rearranged to phyllanthoside (1b).After 4 days the product composition resembled that from phyllanthoside.Discovery of the phyllanthostatin 1 phyllanthoside orthoacid rearrangement revealed a very important aspect of Phyllanthus glycoside chemistry and provided the first examples of O-3 O-4 acetyl migrations in a glucopyranoside.