69985-32-6

Basic information

• Product Name: (S)-4-BENZYLOXY-1,2-BUTANEDIOL
• Synonyms: (S)-4-BENZYLOXY-1,2-BUTANEDIOL;(2S)-4-(Benzyloxy)-1,2-butanediol;(S)-4-(Benzyloxy)butane-1,2-diol;(S)-4-Benzyloxy-1,2-butanediol
• CAS NO: 69985-32-6
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.24
• Product Categories: Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry
• Mol File: 69985-32-6.mol

Chemical Properties

• Boiling Point: 170 °C / 3mmHg
• Flash Point: 175.056oC
• Appearance: /
• Density: 1.12
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -23.0 ° (C=5, EtOH)
• PKA: 14.14±0.20(Predicted)
• CAS DataBase Reference: (S)-4-BENZYLOXY-1,2-BUTANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-BENZYLOXY-1,2-BUTANEDIOL(69985-32-6)
• EPA Substance Registry System: (S)-4-BENZYLOXY-1,2-BUTANEDIOL(69985-32-6)

Safety Data

• Hazardous Substances Data: 69985-32-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-4-BENZYLOXY-1,2-BUTANEDIOL is used as a building block for the preparation of various pharmaceuticals and biologically active molecules. Its unique structure allows it to be a key component in the development of new medications, contributing to the advancement of healthcare solutions.
Used in Organic Synthesis:
In the realm of organic synthesis, (S)-4-BENZYLOXY-1,2-BUTANEDIOL is utilized as a valuable intermediate for the creation of specialty chemicals. Its versatility in chemical reactions makes it an essential tool for synthesizing complex organic compounds.
Used in Medicinal Chemistry:
(S)-4-BENZYLOXY-1,2-BUTANEDIOL has been studied for its potential pharmacological properties, indicating its use in medicinal chemistry for exploring new avenues in drug discovery and development. Its presence in the synthesis of biologically active molecules highlights its importance in creating effective therapeutic agents.

InChI:InChI=1/C11H16O3/c12-8-11(13)6-7-14-9-10-4-2-1-3-5-10/h1-5,11-13H,6-9H2/t11-/m0/s1

Upstream product

• 32233-43-5 2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol 
• 100-44-7 benzyl chloride 
• 82780-39-0 (S)-4-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxolane 
• 78513-07-2 ((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)methanol 
• 161987-40-2 (3S)-(E)-1-(Benzyloxy)-6,6,6-trifluoro-4-hexen-3-ol 
• 70388-33-9 4-benzyloxybut-1-ene 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 71998-69-1 (+/-)-4-benzyloxy-butane-1,2-diol 
• 171110-94-4 4-<(2-benzyloxy)ethyl>-1,3-dioxolan-2-one 
• 177428-61-4 (S)-4-Benzyloxy-2-hydroxy-butyraldehyde 
• 94426-72-9 2-(2-(benzyloxy)ethyl)oxirane 
• 97-93-8 triethylaluminum 
• 78513-15-2 <2R-(2β,3α)>-3-<(phenylmethoxy)methyl>oxiranemethanol 
• 116315-74-3 (R)-4-phenylmethoxybutane-1,2-diyl diacetate 

Downstream Products

• 69985-33-7 (S)-4-Benzyloxy-1,2-dipalmitoylbutan 
• 113522-78-4 (S)-4-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-butan-2-ol 
• 82780-42-5 (S)-4-(2-Benzyloxy-ethyl)-2-((S)-2,3-dimethoxy-propyl)-[1,3]dioxolane 
• 127517-82-2 (S)-3-(benzyloxy)-1-<methyl>propanol 
• 82780-41-4 (S)-4-benzyloxy-1,2-dimethoxy-butane 
• 417717-90-9 (R)-4-Benzyloxy-1-[1,3]dithian-2-yl-butan-2-ol 
• 173279-16-8 (S)-4-Benzyloxy-1-[1,3]dithian-2-yl-butan-2-ol 
• 393109-24-5 2,2-Dimethyl-propionic acid (S)-4-benzyloxy-2-hydroxy-butyl ester 
• 115114-87-9 (2R)-2-(2-benzyloxyethyl)oxirane 
• 69985-32-6 (R)-4-phenylmethoxy-1,2-butanediol 
• 116315-74-3 (R)-4-phenylmethoxybutane-1,2-diyl diacetate 
• 113522-74-0 4-(benzyloxy)-2-methylenebutan-1-ol 
• 113522-77-3 (S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-butyronitrile 
• 113522-75-1 (S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-butylideneamine 

Relevant articles and documents

A convenient synthesis of the enantiomerically pure (S)-2,4-dihydroxybutyl-4-hydroxybenzoate using hydrolytic kinetic resolution

(S)-2,4-Dihydroxybutyl-4-hydroxybenzoate was prepared in an extremely simple and practical way with high enantiomeric excess (99% ee) using Jacobsen’s Hydrolytic Kinetic Resolution technique as a key step and source of chirality.

SILVESTROL ANTIBODY-DRUG CONJUGATES AND METHODS OF USE

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Fused cyclobutanes are found in a range of natural products and formation of these motifs in a straightforward and easy manner represents an interesting synthetic challenge. To this end we investigated an intramolecular variant of the thermal enamine [2 + 2] cyclisation, developing a diastereoselective intramolecular enamine [2 + 2] cyclisation furnishing δ lactone and lactam fused cyclobutenes in good yield and excellent diastereoselectivity.

Carbohydrate-Catalyzed Enantioselective Alkene Diboration: Enhanced Reactivity of 1,2-Bonded Diboron Complexes

Catalytic enantioselective diboration of alkenes is accomplished with readily available carbohydrate-derived catalysts. Mechanistic experiments suggest the intermediacy of 1,2-bonded diboronates.

A concise stereoselective total synthesis of diplodialide C

An asymmetric total synthesis of diplodialide C has been achieved starting from commercially available homoallylic alcohol. Regioselective opening of the chiral epoxide, cross-metathesis reaction, and Yamaguchi macrolactonization were used as the key step

Asymmetric Oxy-Michael Addition to γ-Hydroxy-α,β-Unsaturated Carbonyls Using Formaldehyde as an Oxygen-Centered Nucleophile

Formaldehyde was utilized as an oxygen-centered nucleophile in an asymmetric oxy-Michael addition to γ-hydroxy-α,β-unsaturated carbonyl compounds using bifunctional organocatalysts through hemiacetal intermediates. The cyclic acetal product could be further transformed into β-hydroxycarbonyl compounds, useful synthetic intermediates leading to various important target molecules. As such, this method is an example of a novel formal asymmetric hydration of α,β-unsaturated carbonyl compounds.

A new enantioselective synthesis of the anticonvulsant drug pregabalin (lyrica) based on a hydrolytic kinetic resolution method

A practical and efficient enantioselective synthesis of the anticonvulsant drug pregabalin is described for the first time using Jacobsen's hydrolytic kinetic resolution of a terminal epoxide as a key step and a source of chirality.

MATRIX METALLOPROTEINASE INHIBITORS

The present invention relates to methyl sulfonamides and N-formamides derivatives of formula (I) and to processes for their syntheses. The invention also relates to pharmacological compositions containing these derivatives and methods of treating asthma, rheumatoid arthritis, COPD, rhinitis, osteoarthritis, psoriatie arthritis, psoriasis, pulmonary fibrosis, pulmonary inflammation, acute respiratory distress syndrome, perodontitis, multiple sclerosis, gingivitis, atherosclerosis, dry eye, neointimal proliferation which leads to restenosis and ischemic heart failure, stroke, renal disease, tumor metastasis, and other inflammatory disorders characterized by over expression and over activation of an matrix metalloproteinase using the compounds.

Microbial oxidation of 1,2-diols bearing a substituent with an oxyfunctional group: Preparation of optically active 1,2-diols and α-hydroxy ketones

The preparation of optically active 1,2-diols bearing a substituent with a benzyloxy group at the terminus has been achieved by microbial enantioselective oxidation of the racemic compounds. In the screening test, Ochrobactrum sp. MU2293 was selected as the best strain to perform the enantioselective oxidation of (±)-4-benzyloxybutane-1,2-diol to give the corresponding 4-benzyloxy-1-hydroxybutan-2-one and the remaining (R)-diol with a high ee. This microbial oxidation was applicable to other substrates bearing a substituent with a different carbon number. On the other hand, Bacillus sp. MU2289 catalyzed the oxidation of the 1,2-diols to afford the corresponding α-hydroxy ketones and the (S)-diols as the remaining substrates with the opposite absolute configuration.

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