81703-33-5

Upstream product

• 81653-01-2 (4R,5R)-2,2,4-Trimethyl-5-((E)-1-methyl-2-phenyl-vinyl)-[1,3]dioxolane 
• 81653-01-2 (3R,4S)-3,4-isopropylidenedioxy-2-methyl-1-phenylpent-1-ene 
• 67470-70-6 (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene 
• 1206614-97-2 (4S,5R)-2,2,4-trimethyl-5-[(E)-1-methyl-2-phenylpropenyl]-1,3-dioxolane 
• 1206614-98-3 (4S,5S)-4-[(Z)-2-chloro-1-methyl-2-phenylvinyl]-2,2,5-trimethyl-1,3-dioxolane 
• 91913-82-5 1-((4S,5S)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-ethanol 
• 84519-53-9 (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde 
• 1336854-09-1 biphenyl-4-ylmethyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate 
• 1336854-12-6 (4R,5S)-N-methoxy-N,2,2,5-tetramethyl-1,3-dioxolane-4-carboxamide 
• 676-58-4 methylmagnesium chloride 
• 107983-40-4 (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylic acid 

Downstream Products

• 81653-02-3 C₁₄H₁₉NO₂S 
• 81653-09-0 (3aR,4S,7aR)-6-Ethoxy-4,7a-dimethyl-2-phenyl-3a,6,7,7a-tetrahydro-4H-pyrano[4,3-d]oxazole 
• 81653-03-4 N-[(S)-1-((1R,2S)-1,2-Dihydroxy-propyl)-1-methyl-but-3-enyl]-benzamide 
• 81703-35-7 N-[(R)-1-((1S,2S)-1,2-Dihydroxy-propyl)-1-methyl-but-3-enyl]-benzamide 
• 81653-08-9 N-benzoyl-L-vancosamine 
• 89822-01-5 N-((2S,3S,4S,6S)-3,6-Dihydroxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-benzamide 
• 81653-06-7 N-((2S,3R,4S,6R)-3,6-Dihydroxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-benzamide 
• 81653-07-8 N-((2S,3S,4R,6R)-3,6-Dihydroxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-benzamide 
• 89822-02-6 N-((2S,3S,4R,6S)-3,6-Dihydroxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-benzamide 
• 74966-76-0 N-((2S,3R,4S,6R)-3-Hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-benzamide 
• 85950-14-7 (6S,7S,8S)-6-benzyloxy-2,6-dimethyl-7,8-isopropylidenedioxynon-1-ene 
• 85950-15-8 (6S,7S,8S)-6-benzyloxy-2,6-dimethylnon-1-ene-7,8-diol 

Relevant academic research and scientific papers

Scalable synthesis of enantiomerically pure syn -2,3-dihydroxybutyrate by sharpless asymmetric dihydroxylation of p -phenylbenzyl crotonate

An efficient four-step synthetic route to the useful chiral building block (2R,3S)-dihydroxybutyric acid acetonide in >95% ee is detailed. The sequence is readily scaled, requires no chromatography, and allows for efficient recycling of p-phenylbenzyl alcohol, an expedient for enantio- and diastereoenrichment by recrystallization.

Stereochemical course of baker's yeast mediated reduction of the tri- and tetrasubstituted double bonds of substituted cinnamaldehydes

A comprehensive study of the stereochemical course of baker's yeast mediated reduction of substituted cinnamaldehydes is reported. Hydride addition to the β position of β-methylcinnamaldehydes preferentially afforded isomers of (3S)-3-phenylbutan-1-ol. The reduction of (E)-2,3-dimethyl- cinnamaldehyde (15) produced a mixture of (2S,3S)- and (2R,3S)-2-methyl-3- phenylbutan-1-ol (13 and 14), respectively, with 93 % ee. Conversely (Z)-2,3-dimethylcinnamal-dehyde (16) afforded, a mixture of 13 and 14 with 33 % ee. Accordingly, the reduction of trisubstituted β-methylcinnam-aldehydes 34 and 35 proceeded with the same stereochemical preference and with higher enantioselectivity to give (S) 3-phenylbutan-1-ol (37). In addition, deuterium, incorporation and 2H NMR studies demonstrated that the addition of the second hydrogen atom to the a position proceeded with very low stereochemical control and the overall process is formally a mixture of cis/trans hydrogen addition to the double bond. Alternatively, α-methylcinnamaldehyde is reduced to (S)-2-methyl-3-phenylpropan-1-ol (24) with preferential addition of the hydride to the opposite β face with good stereochemical control of the irons addition of hydrogen to the double bond. Wiley-VCH Verlag GmbH & Co. KGaA.

Synthesis of (-)-Frontalin from the (2S,3R)-Diol prepared from α-Methylcinnamaldehyde and Fermenting Baker's Yeast

The synthesis of (-)-frontalin (13) from the (2S,3R)-diol (2b), through the intermediacy of the C5 (3S,4S) methyl ketone (6) and of the C11 adduct (8), is reported.

THE ABSOLUTE CONFIGURATION OF THE SIDE CHAIN DIOL MOIETY OF THE POISON-FROG ALKALOID PUMILIOTOXIN B

The absolute configuration of the diol moiety in the side chain of pumiliotoxin B has been established by comparison of the ozonolysis product from pumiliotoxin B diacetate with the synthetic 3,4-diacetoxy-2-pentanone derived from L-(+)-tartaric acid.This indicates the absolute configuration (R,R) of C-15, C-16 diol of pumiliotoxin B.

SYNTHESIS OF THE N-BENZOYL DERIVATIVES OF L-ARABINO,L-XYLO AND L-LYXO (L-VANCOSAMINE) ISOMERS OF 2,3,6-TRIDEOXY-3-C-METHYL-3-AMINOHEXOSE FROM A NON-CARBOHYDRATE PRECURSOR

The synthesis of the N-benzoyl derivatives of L-arabino (10),L-xylo (13) and L-lyxo (L-vancosamine) (12) 2,3,6-trideoxy-3-C-methyl-3-aminohexose from the (2S,3R) diol (1) prepared in fermenting bakers' yeast from α-methylcinnamaldehyde and acetaldehyde is reported.