219746-02-8

Upstream product

• 53104-32-8 (5-amino-2,2-dimethyl-1,3-dioxan-5-yl)methanol 
• 126178-04-9 [(S)-4-Benzyl-2,2-dimethyl-[1,3]dioxan-(5E)-ylidene]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 100-39-0 benzyl bromide 
• 3587-60-8 Benzyloxymethyl chloride 
• 126178-04-9 [(S)-4-Benzyl-2,2-dimethyl-[1,3]dioxan-(5Z)-ylidene]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 126178-07-2 (S)-(+)-1-(2,2-dimethyl-1,3-dioxan-5-ylidenamino)-2-methoxymethylpyrrolidine 
• 74181-34-3 2,2,-dimethyl-1,3-dioxan-5-one 

Downstream Products

• 235098-86-9 (4S,6S)-4-((4R,6S)-6-Benzyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-6-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-one 
• 235098-87-0 C₂₈H₃₈O₅ 
• 235098-84-7 4-Nitro-benzenesulfonic acid (4R,6S)-6-benzyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl ester 
• 235098-89-2 C₂₁H₃₁IO₄ 
• 235098-88-1 [(4R,6S)-6-((4R,6S)-6-Benzyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-methanol 
• 235098-93-8 dithiocarbonic acid O-(4-benzyl-6-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl) ester S-methyl ester 
• 219746-26-6 (4S,6R)-4-benzyl-6-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxane 
• 235098-83-6 [(4R,6S)-6-benzyl-2,2-dimethyl-1,3-dioxan-4-yl]methanol 
• 235098-85-8 (4S,6R)-4-Benzyl-6-iodomethyl-2,2-dimethyl-[1,3]dioxane 
• 235098-92-7 (4S,6S)-4-Benzyl-6-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-ol 

Relevant academic research and scientific papers

Preparation and reactions of 2,2-dimethyl-1,3-dioxan-5-one-SAMP-hydrazone: A versatile chiral dihydroxyacetone equivalent

The SAMP-hydrazone of 2,2-dimethyl-1,3-dioxan-5-one represents a valuable chiral dihydroxyacetone equivalent. Asymmetric mono- or α,α′-bisalkylations followed by auxiliary cleavage leads to the corresponding mono- or α,α′-disubstituted, acetonide protected ketodiols in excellent diastereo- and enantiomeric excesses.

Iterative asymmetric synthesis of protected anti-1,3-polyols

A new general method for the iterative asymmetric synthesis of anti-1,3-polyol chains has been developed. The α,α'-bisalkylation of 2,2-dimethyl-1,3-dioxan-5-one SAMP-hydrazone 1 with benzyloxymethylchloride as the second electrophile leads to virtually diastereo- and enantiopure substituted 2,2-dimethyl-1,3-dioxan-5-ones with good overall yields. Their deoxygenation and conversion into primary iodides affords the electrophile for the further alkylation of 1. In this way the configurations of all new stereogenic centres are controlled by a single auxiliary.