138436-28-9

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 226926-94-9 Acetic acid (E)-(R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-methyl-hex-3-enyl ester 
• 88023-78-3 para-methoxybenzyl chloride 
• 138513-53-8 (R)-(E)-2-<<(tert-Butyldimethylsilyl)oxy>methyl>-5-methylhex-3-en-1-ol 
• 152669-39-1 (R)-3-<<(t-butyldimethyl)silyl>oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-1-propanol 
• 138436-23-4 (R)-(E)-1-<(tert-Butyldimethylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-methylhex-3-ene 

Downstream Products

• 140479-42-1 (2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol 
• 140479-45-4 (2R,3S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol 
• 152996-70-8 (2S,3R)-N-Benzyloxy-2-(4-methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-butyramide 
• 152996-68-4 (2R,3R)-1-<<(t-butyldimethyl)silyl>oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-3-<(tri-i-propylsilyl)oxy>butane 
• 152996-69-5 (2S,3R)-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-3-<(tri-i-propylsilyl)oxy>butan-1-ol 
• 152996-67-3 (2R,3R)-4-<<(t-butyldimethyl)silyl>oxy>-3-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-2-butanol 

Relevant academic research and scientific papers

Chemoenzymatic Preparation of a Key Intermediate for Carbapenem Synthesis Starting from Asymmetrized Bis(hydroxymethyl)acetaldehyde (BHYMA)

4-Unsubstituted 2-azetidinones 3a,b, which are useful intermediates for the synthesis of carbapenem abtibiotics, have been enantiospecifically and diastereoselectively prepared starting from asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA) 4, a new chiral building block obtained through biological methods.The key steps are the highly diastereoselective addition of Me2CuLi to 4 (diast. ratio = 95 : 5), and the regioselective deblocking of tBuMe2Si ether in the presence of a (iPr)3Si ether, by using a novel methodology.

Chemoenzymatic Preparation of Asymmetrized Tris(hydroxymethyl)methane (THYM*) and of Asymmetrized Bis(hydroxymethyl)acetaldehyde (BHYMA*) as New Highly Versatile Chiral Building Blocks

A series of asymmetrized tris(hydroxymethyl)methanes 2 and bis(hydroxymethyl)acetaldehydes 3 have been prepared in both enantiomeric forms through a chemoenzymatic methodology.The key step is the highly enantioselective PPL-catalyzed monohydrolysis of 2(E)-alkenyl-1,3-diacetoxypropanes 25-27.A careful study on the effect of unsaturations adjacent to the prochiral center in a series of 2-substituted 1,3-diacetoxypropanes has confirmed the suggested beneficial effect of a ? system in that position but has also unveiled an unprecedented dramatic effect of double-bond configuration on enantioselectivity.A new empirical model for the interpretation of these and other results, based both on polarity and steric arguments, is proposed.This study provides a general protocol for the efficient synthesis of asymmetrized 1,3-propanediols bearing in position 2 saturated or unsaturated carbon chains.

Protecting group controlled diastereoselective allylation of asymmetrized bis (hydroxymethyl) acetaldehydes (BHYMA)

MgBr2 catalysed allylation of a series of diprotected asymmetrized bis (Hydroxymethyl) acetaldehydes 2 with allyltributylstannane proceeds with good diastereoselectivity. The stereochemical results are in line with a cyclic chelated transition state, where only one of the two CH2OR appendages, due to the different nature of protecting groups, is capable of coordinating the Lewis acid.