96149-47-2

Upstream product

• 98-88-4 benzoyl chloride 
• 53735-98-1 (1S,2S)-1,2-bis[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol 
• 50-70-4 D-sorbitol 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 69-65-8 mannitol 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 7462-38-6 O³,O⁴-dibenzoyl-D-mannitol 
• 189702-36-1 (1S,2S,3R)-3,4-Bis-benzyloxymethoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butane-1,2-diol 
• 189702-37-2 Benzoic acid (1S,2R)-2,3-bis-benzyloxymethoxy-1-[(R)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-propyl ester 
• 189702-38-3 Benzoic acid (1S,2R,3R)-3,4-bis-benzyloxymethoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-butyl ester 
• 189702-24-7 Benzoic acid (1R,3R)-3,4-bis-benzyloxymethoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-oxo-butyl ester 
• 189702-19-0 Benzoic acid (1R,2R)-2,3-bis-benzyloxymethoxy-1-((R)-2,2-dimethyl-[1,3]dioxolane-4-carbonyl)-propyl ester 
• 1054632-39-1 C₃₉H₄₂O₁₀ 
• 1202372-99-3 1,2,5,6-tetra-O-acetyl-3,4-di-O-benzoyl-D-mannitol 
• 897954-00-6 C₂₂H₂₂O₇ 
• 1357379-95-3 1,2-dideoxy-5,6-O-(1-methylethylidene)-D-arabino-hex-1-enitol 3,4-dibenzoate 

Relevant academic research and scientific papers

Total synthesis of (-)-cleistenolide

An efficient and short total synthesis of (-)-cleistenolide (1) from D-mannitol with an overall yield of 23.6% is described. The chiron approach for the synthesis of (-)-cleistenolide involves a one-C-atom Wittig olefination, a selective allylic triethylsilyl protection, and a Grubbs-catalyzed ring-closure-metathesis (RCM) reaction as the key steps. Copyright

Studies directed toward the first total synthesis of acremodiol and acremonol

Studies directed toward the synthesis of acremodiol and acremonol resulted in the synthesis of two macrodiolides 1, 1a, and 2 besides 3. The attempted synthesis of 1 and 2 confirmed that the absolute stereochemistry defined in the earlier report is incorr

Diastereoselective Grignard Additions to O-Protected Polyhydroxylated Ketones: A Reaction Controlled by Groundstate Conformation?

The O-protected polyhydroxy ketones 9-14 and 39, 42 add σ-type Grignard reagents with >90:10 stereoselectivity to give the 3,4-syn-adducts 17-22 and 43, 45, respectively, as the major diastereomers (Tables 1 and 2). The stereoselectivity is interpreted in terms of early transition states which are very close to the groundstate conformations shown in Figure 6 and 7. These demonstrate that the "top face" of the carbonyl group is much less shielded than the "bottom" face, Complexation phenomena are of minor importance. It is also shown that the classical transition state models (Felkin-Anh or chelate Cram) are not applicable to polyoxygenated ketones.

New Chiral Building Blocks from 1,2;5,6-Di-O-isopropylidene-D-mannitol: Synthesis of C2-Symmetrical and Unsymmetrical Mono- and Bisepoxides and of a Polyhydroxylated Butenolide

The enantiopure epoxides 2-6 were synthesized from 1,2;5,6-di-O-isopropylidene-D-mannitol (1).The terminal epoxides 2 and 3 are available from the desoxy mannitol 9 in three steps.The C2-symmetrical epoxides 4 and 5 were generated via the C-4-inverted alcohol 15.The C2-symmetrical bisepoxide 6 was prepared in a short sequence maintaining the symmetry throughout the entire synthesis.The crystalline butenolide 44 was prepared in five steps from 1 by Wittig olefination and lactonization. - Key Words: Epoxides, C2-symmetrical / Bisepoxides / Butenolide, polyhydroxylated

SYNTHESIS OF (3R,4R)-1,5-HEXADIEN-3,4,-DIOL AND ITS UNSYMMETRICAL DERIVATIVES : APPLICATION TO (R)-(+)-α-LIPOIC ACID

(3R,4R)-1,5-Hexadien-3,4-diol and its umsymmetrical derivatives were prepared starting from D-mannitol and their utility in the synthesis of (R)-(+)-α-lipoic acid has been explored.

SOME ASPECTS OF THE ISOPROPYLIDENATION OF D-GLUCITOL UNDER NEUTRAL CONDITIONS

Isopropylidenation of D-glucitol (1) under neutral conditions, by treatment with 2,2-dimethoxypropane in 1,2-dimethoxyethane, has been studied.An improved procedure for the isolation of 1,2:5,6-di-O-isopropylidene-D-glucitol, the main equilibrium product, by direct crystallisation or via the 3,4-dibenzoate is described.Some aspects of the reaction are discussed and compared with results obtained previously from the isopropylidenation of 1 in the presence of zinc chloride.