381247-05-8

Basic information

• Product Name: (R)-2-Benzyloxymethoxy-3-methyl-butyric acid methyl ester
• Synonyms: (R)-2-Benzyloxymethoxy-3-methyl-butyric acid methyl ester
• CAS NO: 381247-05-8
• Molecular Weight: 252.31
• Mol File: 381247-05-8.mol

Chemical Properties

• CAS DataBase Reference: (R)-2-Benzyloxymethoxy-3-methyl-butyric acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Benzyloxymethoxy-3-methyl-butyric acid methyl ester(381247-05-8)
• EPA Substance Registry System: (R)-2-Benzyloxymethoxy-3-methyl-butyric acid methyl ester(381247-05-8)

Safety Data

• Hazardous Substances Data: 381247-05-8(Hazardous Substances Data)

Upstream product

• 640-68-6 D-Val-OH 
• 17407-56-6 (R)-2-Hydroxy-3-methylbutyric acid 
• 3587-60-8 Benzyloxymethyl chloride 
• 90244-32-9 (R)-methyl 2-hydroxy-3-methylbutanoate 

Downstream Products

• 381246-83-9 (4R,5S,6R)-4-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-6-(tert-butyldiphenylsilanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxane 
• 381246-77-1 2,2-dimethylpropionic acid (2S,3R,4R)-4-benzyloxymethoxy-2-(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl ester 
• 381247-07-0 (2S,3R,4R)-4-Benzyloxymethoxy-2-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexanoic acid methyl ester 
• 381247-08-1 (2S,3R,4R)-4-Benzyloxymethoxy-2-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexan-1-ol 
• 183201-71-0 (2S,3S,4R)-4-benzyloxymethoxy-2-hydroxy-3,5-dimethylhexanoic acid methyl ester 
• 381246-75-9 (E)-(4R)-4-benzyloxymethoxy-5-methylhex-2-enoic acid methyl ester 
• 160741-81-1 (2S,3S,4R)-2-hydroxy-3-methyl-4-iso-propyl-4-butyrolactone 
• 381246-76-0 (3S,4R)-4-benzyloxymethoxy-3,5-dimethylhexanoic acid methyl ester 
• 906534-74-5 (R)-2-Benzyloxymethoxy-3-methyl-butyraldehyde 
• 1026340-90-8 (E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid 1-methylcyclopentyl ester 
• 1027032-49-0 (E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid 2,2-dimethylpropyl ester 

Relevant articles and documents

Iterative synthesis of deoxypropionate units: The inductor effect in acyclic conformation design

Conjugate addition of lithium dimethylcuprate to acyclic α,β-unsaturated esters of varying lengths bearing terminal alkyl or phenyl groups leads to a preponderance of syn 1,3-adducts when one methyl is already present. Conversion to enoates, and iteration of cuprate additions also favors syn adducts to give contiguous deoxypropionate units in a growing chain. The effect of end-group variation (Me, i-Pr, phenyl, tert-butyl) in conjunction with the nature of the ester group (Me, tert-butyl, etc.) on the diastereoselectivity of syn and anti products was studied. The results are rationalized in terms of inductor effects related to the minimization of the 1,5-pentane interactions in energetically favored folded conformations and corroborated by homodecoupling NMR studies.

Total synthesis of bafilomycin A1 relying on iterative 1,2-induction in acyclic precursors

The macrolide bafilomycin A1 was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A1 via a conventional carbodiimide-mediated Keck-type macrolactonization.