290836-45-2

Upstream product

• 3969-59-3 mannitol triacetonide 
• 98-88-4 benzoyl chloride 
• 38145-93-6 1,2:3,4-di-O-isopropylidene-D-mannitol 

Downstream Products

• 290334-86-0 4-(1-benzyloxypentyl)-2,2-dimethyl-5-oxiranyl[1,3]dioxolane 
• 290334-91-7 1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]ethane-1,2-diol 
• 290334-84-8 5-benzyloxy-1,2:3,4-di-O-isopropylidenenonane 
• 290334-87-1 1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]pent-4-en-1-ol 
• 290334-88-2 6-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]tetrahydropyran-2-one 
• 290334-92-8 1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]pentane-1,5-diol 
• 290334-85-9 Toluene-4-sulfonic acid (R)-2-[(4R,5R)-5-((S)-1-benzyloxy-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-ethyl ester 
• 540727-82-0 3-benzenesulfonyl-1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]-5-(tert-butyldimethylsilanyloxy)pentan-1-ol 
• 1307864-65-8 C₃₅H₄₄O₇Si 
• 1307864-66-9 C₃₂H₄₀O₇Si 
• 1307864-64-7 (R)-2-(tert-butyldiphenylsilyloxy)-2-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethylbenzoate 
• 1384962-76-8 tert-butyldiphenyl ((S)-1-((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)allyloxy)silane 
• 1384962-74-6 (R)-1-((4R,5S)-5-((S)-1-(tert-butyldiphenylsilyloxy)allyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol 
• 1384962-77-9 C₃₃H₄₂O₇SSi 

Relevant academic research and scientific papers

Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide

Total synthesis of (+)-boronolide, (+)-deacetylboronolide, and (+)-dideacetylboronolide has been achieved from a single intermediate 26, which was synthesized in 11 steps from a D-mannitol-derived intermediate 8 in an overall yield of 10%. The key steps in the synthesis are inversion of a chiral center by taking an advantage of the inherent mechanism involved in the ring closing to an epoxide via intramolecular SN2 reaction and lactonization of a diol using Fetizons reagent. The strategy is amenable to preparation of analogues of (+)-boronolide in sufficient amount for further screening of biological activity.

Total synthesis of (-)-cleistenolide

The total synthesis of (-)-cleistenolide, a novel natural product recently isolated from the annonaceae species cleistochlamys kirkii oliver, is described. The synthesis proceeds starting from easily accessible d-manitol using a selective benzoylation, a

Formal total synthesis of (+)-boronolide

(+)-Boronolide, a polyacetoxy natural product having four contiguous asymmetric centers has been synthesized from D-mannitol. (C) 2000 Elsevier Science Ltd.