1374646-22-6

Basic information

• Product Name: (3R,4S)-6-phenylhex-1-ene-3,4-diol
• Synonyms: (3R,4S)-6-phenylhex-1-ene-3,4-diol
• CAS NO: 1374646-22-6
• Molecular Weight: 192.258
• Mol File: 1374646-22-6.mol

Chemical Properties

• CAS DataBase Reference: (3R,4S)-6-phenylhex-1-ene-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-6-phenylhex-1-ene-3,4-diol(1374646-22-6)
• EPA Substance Registry System: (3R,4S)-6-phenylhex-1-ene-3,4-diol(1374646-22-6)

Safety Data

• Hazardous Substances Data: 1374646-22-6(Hazardous Substances Data)

Upstream product

• 10374-29-5 N-benzylidenebenzamide 
• 104-53-0 3-phenyl-propionaldehyde 
• 37904-38-4 (3S)-5-phenyl-1-penten-3-ol 
• 1374646-37-3 (S,e)-6-(3-nitrophenoxy)-1-phenylhex-4-en-3-ol 
• 1329020-55-4 C₁₃H₁₉BO₂ 

Relevant articles and documents

Enantio- and Diastereoselective Synthesis of 1,5-syn-(Z)-Amino Alcohols via Imine Double Allylboration: Synthesis of trans-1,2,3,6-Tetrahydropyridines and Total Synthesis of Andrachcine

A stereoselective synthesis of trans-1,2,3,6-tetrahydropyridines 8 is described. This synthesis proceeds via intramolecular Mistunobu reactions of 1,5-syn-(Z)-amino alcohols 7, which were prepared by a highly diastereo- and enantioselective double-allylboration reaction of aldehyde 5 and silylimine 6. The chiral bifunctional γ-borylallylborane 9E was generated in situ by hydroboration of allene 3 with (diisopinocampheyl)borane 4. This strategy was applied to the total synthesis of andrachcine 1, thus establishing with certainty the absolute and relative configuration of the natural product.

Iterative asymmetric allylic substitutions: Syn- and anti-1,2-diols through catalyst control

A copper-catalyzed asymmetric allylic boronation (AAB) gives access to syn- and anti-1,2-diols. The method facilitates an iterative strategy for the preparation of polyols (see scheme), such as the fully differentiated L-ribo-tetrol and protected D-arabin

Development of a double allylboration reagent targeting 1,5-syn-(E)-diols: Application to the synthesis of the C(23)-C(40) fragment of tetrafibricin

Interest in the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42, and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% ee), diastereoselectivity (dr >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin.