101020-38-6

Basic information

• Product Name: (E)-4-benzyloxy-2-methyl-2-butenoic acid ethyl ester
• Synonyms: (E)-4-benzyloxy-2-methyl-2-butenoic acid ethyl ester
• CAS NO: 101020-38-6
• Molecular Weight: 234.295
• Mol File: 101020-38-6.mol

Chemical Properties

• CAS DataBase Reference: (E)-4-benzyloxy-2-methyl-2-butenoic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-benzyloxy-2-methyl-2-butenoic acid ethyl ester(101020-38-6)
• EPA Substance Registry System: (E)-4-benzyloxy-2-methyl-2-butenoic acid ethyl ester(101020-38-6)

Safety Data

• Hazardous Substances Data: 101020-38-6(Hazardous Substances Data)

Upstream product

• 60656-87-3 benzyloxyacetoaldehyde 
• 107905-52-2 ethyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate 
• 67468-80-8 2-(Triphenyl-λ⁴-phosphanyl)-propionic acid ethyl ester 
• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 
• 3699-66-9 ethyl 2-diethoxyphosphorylpropionate 
• 100-39-0 benzyl bromide 
• 622-08-2 2-Benzyloxyethanol 
• 68972-96-3 (Z)-1,4-dibenzyloxy-2-butene 
• 68973-05-7 (2R*,3S*)-2,3-bis((benzyloxy)methyl)oxirane 

Downstream Products

• 115827-26-4 (2Z)-4-(benzyloxy)-2-methylbut-2-en-1-ol 
• 115936-20-4 [(2S,3R)-3-[(benzyloxy)methyl]-2-methyloxiran-2-yl]methanol 
• 115827-34-4 (E)-(S)-6-Benzyloxy-4,4-dimethyl-hex-2-ene-1,5-diol 
• 132409-53-1 (E)-(5S)-6-(benzyloxy)-4-methyl-1,3-hexadien-5-ol 
• 115827-41-3 (E)-(2S,5S)-6-(benzyloxy)-2,4-dimethyl-3-hexene-1,5-diol 
• 115827-35-5 (E)-(2R,5S)-6-(benzyloxy)-2,4-dimethyl-3-hexene-1,5-diol 
• 115827-32-2 (R)-2-Benzyloxy-1-((R)-2-methyl-2,5-dihydro-furan-2-yl)-ethanol 
• 101020-39-7 (2R,3S)-4-(benzyloxy)-2,3-epoxy-2-methylbutan-1-ol 
• 115827-28-6 (2R,3R)-3-Benzyloxymethyl-2-methyl-oxirane-2-carbaldehyde 
• 115936-22-6 (Z)-(4S,5R)-6-(benzyloxy)-4,5-epoxy-4-methyl-2-hexen-1-ol 
• 115827-30-0 (E)-(4S,5R)-6-(benzyloxy)-4,5-epoxy-4-methyl-2-hexenol 
• 115936-21-5 (Z)-(4S,5R)-ethyl 6-(benzyloxy)-4,5-epoxy-4-methyl-2-hexenoate 
• 115827-29-7 (E)-(4S,5R)-ethyl 6-(benzyloxy)-4,5-epoxy-4-methyl-2-hexenoate 
• 115827-31-1 (Z)-(4S,5R)-6-(benzyloxy)1-<(tert-butyldimethylsilyl)-oxy>-4,5-epoxy-4-methyl-2-hexane 

Relevant articles and documents

BIARYL DERIVATIVES AS GPR120 AGONISTS

The present invention relates to biaryl derivatives of Formula 1, a method for preparing the same, a pharmaceutical composition comprising the same and use thereof. The biaryl derivatives of Formula 1 according to the present invention promote GLP-1 formation in the gastrointestinal tract and improve insulin resistance in the liver or in muscle due to anti-inflammatory action in macrophages, lipocytes, etc., and can accordingly be effectively used for preventing or treating diabetes, complications of diabetes, obesity, non-alcoholic fatty liver, steatohepatitis, osteoporosis or inflammation.

Acyclic Stereoselection in the Ortho Ester Claisen Rearrangement

The ortho ester Claisen rearrangement of trisubstituted allylic alcohols exhibits significant levels of diastereoselection. In E allylic alcohols, a 1,3-diaxial interaction develops in the chairlike transition state leading to the anti isomer, rendering the reaction syn selective by a factor of 3-5 to 1. In Z allylic alcohols, the 1,3-diaxial interaction develops in the transition state leading to the syn isomer, generating an anti:syn selectivity of 6-15 to 1. The relative stereochemistry of the syn isomer was confirmed independently by the synthesis of the mycotoxin botryodiplodin.

Stereochemistry of SN2' Additions to Acyclic Vinyloxiranes

The isomeric trans-(E)-, trans-(Z)-, cis-(E)-, and cis-(Z)-vinyloxiranes 7,9,17 and 19 were prepared from 2-(benzyloxy)ethanol by sequential Swern-Wittig or Swern-Horner-Emmons propionate condensation, DIBAH reduction, Sharpless epoxidation, Swern oxidation, Wittig or Horner-Emmons acetate condensation, and a second DIBAH reduction.Addition of lithium dimethylcuprate and lithium methylcyanocuprate to these epoxides in THF-eather at -20 to 0 deg C afforded the allylic alcohols 22,25, ent-23, and ent-22 as the major products.These products are formed by anti addition to the lower energy conformer (s-trans for 7,17, and 19 and s-cis for 9) of the respective vinyloxirane.The conformational preferences of transition-state-like geometries of the vinyl-oxiranes, calculated with the aid of Still's MACROMODEL program, were in agreement with the observed trends.

A CONVENIENT PREPARATION OF 2-BENZYLOXYACETALDEHYDE

Two new and convenient routes to 2-benzyloxyacetaldehyde (4) that involve oxidative cleavage of (Z)-1,4-dibenzyloxy-2-butene (2) are described.

AN ENANTIOSELECTIVE SYNTHESIS OF THE CARZINOPHILIN DEGRADATION PRODUCT (2S,3S) 4-AMINO-2,3-DIHYDROXY-3-METHYLBUTYRIC ACID

An efficient, enantioselective synthesis of (2S,3S) 4-amino-2,3-dihydroxy-3-methylbutyric acid (1) is described.The sequence includes the direct use of azide to selectively open a secondary epoxy alcohol formed under Payne rearrangement conditions.