147849-63-6

Basic information

• Product Name: (5R)-5-Hydroxy-3-oxo-6-(benzyloxy)-hexanoic Acid tert-Butyl Ester
• Synonyms: (5R)-5-Hydroxy-3-oxo-6-(benzyloxy)-hexanoic Acid tert-Butyl Ester;VBXDDEFKXNFJLL-OAHLLOKOSA-N
• CAS NO: 147849-63-6
• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.36946
• Product Categories: Aromatics, Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 147849-63-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: (5R)-5-Hydroxy-3-oxo-6-(benzyloxy)-hexanoic Acid tert-Butyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (5R)-5-Hydroxy-3-oxo-6-(benzyloxy)-hexanoic Acid tert-Butyl Ester(147849-63-6)
• EPA Substance Registry System: (5R)-5-Hydroxy-3-oxo-6-(benzyloxy)-hexanoic Acid tert-Butyl Ester(147849-63-6)

Safety Data

• Hazardous Substances Data: 147849-63-6(Hazardous Substances Data)

Usage

Uses

(5R)-5-Hydroxy-3-oxo-6-(benzyloxy)-hexanoic Acid tert-Butyl Ester is used in the preparation of antifungal macrolide antibiotic (+)-Roxaticin, Phorboxazole B and Bryostatin 2.

Upstream product

• 60656-87-3 benzyloxyacetoaldehyde 
• 146431-18-7 (Z)-1,3-bis(trimethylsiloxy)-1-tert-butoxybuta-1,3-diene 
• 147849-58-9 tert-Butyl (R)-4-benzyloxy-3-hydroxybutanoate 
• 147849-59-0 tert-Butyl (S)-4-benzyloxy-3-hydroxybutanoate 
• 95967-46-7 tert-Butyl 4-benzyloxy-3-oxobutanoate 
• 32122-09-1 ethyl benzyloxyacetate 
• 540-88-5 acetic acid tert-butyl ester 
• 106058-91-7 (+)-(R)-ethyl 4-benzyloxy-3-hydroxybutanoate 
• 147849-60-3 Methyl (S)-4-(benzyloxy)-3-hydroxybutanoate 
• 114784-19-9 (R)-Methyl 4-benzyloxy-3-hydroxybutanoate 

Downstream Products

• 153255-54-0 (4R,6R)-6-Benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-one 
• 310883-86-4 (4R,6R)-6-hydroxymethyl-4-methoxy-tetrahydro-2H-pyran-2-one 
• 296785-16-5 (4R,6R)-6-(benzyloxymethyl)-4-methoxy-tetrahydro-2H-pyran-2-one 
• 296785-20-1 (2S,4R,6R)-2-[4-((E)-2-[(2R,3S,4S,5S,6R)-3,5-dimethyl-6-(2-trimethylsilyloxyethyl)-4-triphenylsilyloxy-tetrahydro-2H-pyran-2-yl]prop-1-enyl)(1,3-oxazol-2-yl)]methyl-4-methoxy-6-triethylsilyloxymethyl-tetrahydro-2H-pyran-2-ol 
• 296795-40-9 (9R)-9-(benzyloxymethyl)-1,4,8-trioxaspiro[4.5]decan-7-ol 
• 310883-88-6 (2R,4R,6R)-2-[4-((E)-2-[(2R,3S,4S,5S,6R)-3,5-dimethyl-6-[2-(trimethylsilyloxyethyl)]-4-(triphenylsilyloxy)-tetrahydro-2H-pyran-2-yl]prop-1-enyl)(1,3-oxazol-2-yl)]-methyl-4-methoxy-2-(triethylsilyloxy)-6-(triethylsilyloxymethyl)-tetrahydro-2H-pyran-2-ol 
• 215876-09-8 (3R,5R)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester 
• 549502-23-0 (3S,5R)-6-benzyloxy-3,5-dihydroxy-hexanoic acid tert-butyl ester 
• 215876-23-6 C₇₇H₁₂₉NO₁₂Si₄ 

Relevant articles and documents

Diastereoselective synthesis of syn-3,5-dihydroxyesters via ruthenium-catalyzed asymmetric transfer hydrogenation

The asymmetric transfer hydrogenation of chiral 5-hydroxy-3-ketoesters in 2-propanol using chlororuthenium(II)arene/β-amino alcohol in situ catalyst combinations or a pre-synthesized Ru-{β-amino alcohol} true catalyst, provides syn-3,5-dihydroxyesters in

Synthesis of ethyl and t-butyl (3R,5S)-dihydroxy-6-benzyloxy hexanoates via diastereo- and enantioselective microbial reduction

Previously we have demonstrated the reduction of ethyl diketoester 4 to the corresponding dihydroxy ester 6a by Acinetobacter sp. SC13874. Recently we screened more than 100 cultures for microbial reduction of both the ethyl and t-butyl diketoesters 4 and

Asymmetric Hydrogenation of 3,5-Dioxoesters Catalyzed by Ru-binap Complex: A Short Step Asymmetric Synthesis of 6-Substituted 5,6-dihydro-2-pyrones

Asymmetric hydrogenation of 3,5-dioxoesters 1a-c using Ru2Cl4((R) or (S)-binap)2(NEt3) as the catalyst gave dominantly anti 3,5-dihydroxyesters 2, which were then converted into unsaturated lactones 5a-b (ca. 80percent e.e.).The pathway of the hydrogenation reaction was also investigated by asymmetric hydrogenation of (R)- or (S)-5-hydroxy-3-oxoesters 8a-c.It was revealed that the Ru-binap catalyzed hydrogenation of 1a-b proceed dominantly via the β-diketone mode.A convenient asymmetric synthesis of hydroxylactone 3c and unsaturated lactone 5c was presented.Key words: 3,5-dioxoester; Ru-binap catalyst; asymmetric hydrogenation; asymmetric synthesis; lactone