14125-71-4

Upstream product

• 143995-54-4 2,3-di-O-acetyl-4,6-o-benzylidene-α-D-glucopyranosyl bromide 
• 108-24-7 acetic anhydride 
• 2880-96-8 methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside 
• 257925-66-9 acetyl 2,3-di-O-acetyl-4,6-O-benzyliden-D-glucopyranoside 

Downstream Products

• 110522-31-1 Acetic acid (4aR,6R,7S,8S,8aR)-6,7-dichloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 110522-29-7 4-chlorobutyl 3-O-acetyl-4,6-O-benzylidene-2-chloro-2-deoxy-α-D-mannopyranoside 
• 110522-30-0 Acetic acid (4aR,6R,7R,8S,8aR)-7-chloro-6-(4-chloro-butoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 124061-91-2 (4S,5R)-4-((E)-Buta-1,3-dienyl)-2-phenyl-[1,3]dioxan-5-ol 
• 110522-35-5 Acetic acid (4aR,6S,7S,8S,8aR)-6,7-dichloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 110522-31-1 Acetic acid (4aR,6S,7R,8S,8aR)-6,7-dichloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 110522-36-6 Acetic acid (4aR,6R,7R,8S,8aR)-6,7-dichloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 124061-99-0 Acetic acid (4S,5R)-4-((E)-buta-1,3-dienyl)-2-phenyl-[1,3]dioxan-5-yl ester 
• 124062-01-7 (4S,5R)-4-((E)-Buta-1,3-dienyl)-5-methoxy-2-phenyl-[1,3]dioxane 
• 124062-00-6 Methanesulfonic acid (4S,5R)-4-((E)-buta-1,3-dienyl)-2-phenyl-[1,3]dioxan-5-yl ester 
• 124061-95-6 (3aR,7aR,11aS,11bR,11cS)-6a-Hydroxy-4-oxo-10-phenyl-3,3a,4,5,6,6a,7a,8,11a,11b-decahydro-7,9,11-trioxa-benzo[de]anthracene-11c-carboxylic acid methyl ester 
• 124061-92-3 (4aS,5R,8aS)-5-((4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-1,4-dioxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester 
• 124061-94-5 (3aR,7aR,11aS,11bR,11cS)-4-Oxo-10-phenyl-3,3a,4,5,7a,8,11a,11b-octahydro-7,9,11-trioxa-benzo[de]anthracene-11c-carboxylic acid methyl ester 
• 124061-96-7 (4aS,5R,8aR)-5-((4S,5R)-5-Acetoxy-2-phenyl-[1,3]dioxan-4-yl)-1,4-dioxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Rapid preparation of variously protected glycals using titanium(III)

Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)2. This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. β-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.

Variously substituted glycals are readily prepared from glycosyl bromides using (Cp2TiCl)2

Glycosyl halides, variously substituted with ether, acetal, or ester protecting groups, were converted to the corresponding glycals in high yield by reaction with (Cp2TiCl)2. A glycosyl chloride was less reactive than the analogous bromide.

An Approach to the Total Synthesis of the Prelog-Djerassi Lactone

An approach to the synthesis of the Prelog-Djerassi lactone using D-glucose as a starting material is described.The use of Swern oxidation provides an efficient means of preparing carbohydrate ketones.An unusual departure from the normal reaction pathway