138436-30-3

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 138436-20-1 (R)-(E)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-5-methylhex-3-en-1-ol 
• 88023-78-3 para-methoxybenzyl chloride 
• 152669-37-9 (R)-3-<<(t-butyldiphenyl)silyl>oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-1-propanol 
• 138436-25-6 (R)-(E)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-methylhex-3-ene 

Downstream Products

• 140479-40-9 (2R,3R)-1-((tert-butyldiphenylsilyl)oxy)-2-((((p-methoxybenzyl)oxy)methoxy)methyl)hex-5-en-3-ol 
• 140479-44-3 (2R,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxymethoxymethyl)-hex-5-en-3-ol 
• 174156-51-5 (2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxymethoxymethyl)-butan-2-ol 
• 174156-52-6 (2R,3R)-3-Benzyloxymethoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-butan-1-ol 
• 1026921-32-3 (2R,3R)-3-Benzyloxymethoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-butyraldehyde 
• 174156-53-7 (4S,5S,6R)-6-Benzyloxymethoxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-hept-1-en-4-ol 
• 146512-61-0 (2S,3R)-2-((((4-methoxybenzyl)oxy)methoxy)methyl)hex-5-ene-1,3-diol 
• 146512-63-2 (4R,5R)-cis-4-allyl-5-((((4-methoxybenzyl)oxy)methoxy)methyl)-2,2-dimethyl-1,3-dioxane 
• 140479-50-1 (2R,3R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)hex-5-ene-1,3-diol 
• 140479-54-5 (4R,5R)-trans-4-allyl-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxane 

Relevant academic research and scientific papers

Synthesis of a key intermediate for Thienamycin and Imipenem through stereoselective two-direction elongation of asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA*)

The enantioselective formal synthesis of Thienamycin and Imipenem has been realised through two-direction elongation of the chiral building block bis(hydroxymethyl)acetaldehyde 5. The generation of the two additional stereocenters has been carried out with excellent diastereoselectivity thanks to two sequential 'protecting group controlled' nucleophilic additions. Another key step was represented by the regioselective oxidation of a primary-secondary 1,3-diol to the corresponding β-hydroxyacid.

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.