97204-83-6

Upstream product

• 198969-39-0 5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 532-20-7 D-Ribose 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 5336-08-3 D-Ribono-1,4-lactone 
• 100-39-0 benzyl bromide 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 116780-31-5 (1R)-1-((4R,5S)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol 
• 19493-09-5 Methylenetriphenylphosphorane 
• 85846-80-6 5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 

Downstream Products

• 257281-17-7 (4S,5S)-4-((R)-1-Allyloxy-2-benzyloxy-ethyl)-2,2-dimethyl-5-vinyl-[1,3]dioxolane 
• 681853-94-1 (+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one 
• 257281-19-9 (3aR,4R,7R,8R,8aS)-4-Benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]oxepine-7,8-diol 
• 257281-18-8 (3aS,4R,8aS)-4-Benzyloxymethyl-2,2-dimethyl-3a,4,6,8a-tetrahydro-[1,3]dioxolo[4,5-c]oxepine 
• 718604-59-2 1-[(4S,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethane-1,2-diol 
• 718604-58-1 2-Benzyloxy-1-[(4S,5S)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethanone 
• 328396-52-7 (2S,3R)-5-benzyl-2,3-O-isopropylidene-4-C-methylene-2-C-vinyl-D-erythro-pentitol 
• 328396-53-8 (4R,5S)-(-)-3-[(benzyloxy)methyl]-4,5-O-isopropylidene-2-cyclopenten-1-ol 
• 495397-67-6 (4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 681853-97-4 1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-(benzyloxymethyl)-2-propen-1-ol 
• 681853-99-6 (1R,4S,5S)-1-(benzyloxymethyl)-2-en-4,5-(O-isopropylidenedioxy)-cyclopentan-1-ol 
• 117307-62-7 (3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one 
• 114948-34-4 (3aS,4S,6aS)-4-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol 
• 97204-84-7 2,5-anhydro-6-O-benzyl-1-iodo-3,4-O-isopropylidene-D-altro-hexitol 

Relevant academic research and scientific papers

Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides

The preparative and stereoselective synthesis (45-50% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions. Copyright Taylor & Francis, Inc.

Preparative Synthesis of the Key Intermediate, (4R,5R)-3-Benzyloxymethyl-4,5-isopropylidenedioxycyclopent-2-enone for Carbocyclic Nucleosides

(4R,5R)-3-Benzyloxymethyl-4,5-isopropylidenedioxycyclopent-2-enone (1), a versatile intermediate for the synthesis of carbocyclic nucleosides was synthesized from D-ribose in 10 steps and 26 percent overall yield.

Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides: Effects of the Bulky Protecting Groups to Enforce Facial Selectivity

The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the

A ring closing metathesis-osmylation approach to oxygenated oxepanes as carbohydrate surrogates

A ring closing metathesis (RCM)-osmylation sequence has been developed for the formation of highly oxygenated cyclic ethers from the corresponding acyclic dienes. A systematic examination of various substrates in this reaction revealed that the process is general in scope and is insensitive to the number of alkoxy substituents present. Subsequent osmylation of the metathesis product proceeds with excellent diastereoselectivity to furnish highly oxygenated oxepanes. These oxepanes represent one-carbon homologated carbohydrates.

ELECTROPHILE-MEDIATED CYCLIZATIONS OF 6-O-BENZYL-1,2-DIDEOXY-3,4-O-ISOPROPYLIDENE-D-ribo-HEX-1-ENITOL TO DERIVATIVES OF 2,5-ANHYDRO-6-O-BENZYL-3,4-O-ISOPROPYLIDENE-D-altro-HEXITOL

Electrophile (bromine, iodine, mercuric acetate, mercuric trifluoroacetate, phenylselenyl chloride)-mediated cyclization of 6-O-benzyl-1,2-dideoxy-3,4-O-isopropylidene-D-ribo-hex-1-enitol (2) led exclusively to 1-substituted derivatives of 2,5-anhydro-6-O