192827-14-8

Upstream product

• 106-24-1 Geraniol 
• 192827-11-5 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranosyl bromide 
• 192827-18-2 geranyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside 
• 14262-83-0 2,3,4-tri-O-benzoyl-α-D-xylopyranosyl bromide 
• 891784-73-9 geranyl 6-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 891784-74-0 geranyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 22850-13-1 geranyl O-β-D-glucopyranoside 
• 104707-01-9 1,2,3,4-tetra-O-benzoyl-β-D-glucopyranose 
• 192827-10-4 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->6)-1,2,3,4-tera-O-benzoyl-β-D-glucopyranose 

Downstream Products

• 150995-11-2 geranyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of naturally occurring geranyl 6-o-glycosyl-β-d-glucopyranosides

Direct β-glucosidation between geranyl alcohol and D-glucose (4) using the immobilized β-glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave geranyl O-β-D-glucoside (1) in 11% yield. The coupling of the geranyl O-β-D-glucopyranoside congener (7) with 2,3,4-tri-O-benzoyl-α-D-xylopyranoside bromide (8) or 2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl bromide (10) afforded the coupled products (9 and 11), respectively. Deprotection of the coupled products (9 and 11) using MeONa in MeOH-THF gave the synthetic geranyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside (2) and geranyl 6-O-α-L-arabinopyranosyl-β-D-glucopyranoside (Kenposide A, 3).

The Role of Diglycosides as Tea Aroma Precursors: Synthesis of Tea Diglycosides and Specificity of Glycosidases in Tea Leaves

Two general synthetic routes were established in order to synthesize two diglycosides, primeverosides (1) and vicianosides (2), found in tea leaves. Procedure 1 is based on the Koenig-Knorr type of condensation of aglycon alcohols and 1-α-bromohexabenzoylprimeverose (6) and is suitable for the condensation of primary alcohols. Procedure 2 is to combine tribenzoyl-β-D-glucoside (8) and 1-α-bromotribenzoylxylose (4). The primeveroside of a tertiary alcohol was synthesized by this method which is also applicable to the synthesis of vicianosides. The hydrolysis rate of each of the 12 synthesized glycosides by a crude tea enzyme was evaluated, which suggest that the main glycosidase is primeverosidase and the enzyme mixture shows substrate specificity to both the carbohydrate and aglycon moieties.