146566-78-1

Basic information

• Product Name: (3S,4S,5S,6S,7S)-6-(benzyloxy)-3,5-dimethyl-4-hydroxy-7,8-(isopropylidenedioxy)oct-1-ene
• Synonyms: (3S,4S,5S,6S,7S)-6-(benzyloxy)-3,5-dimethyl-4-hydroxy-7,8-(isopropylidenedioxy)oct-1-ene
• CAS NO: 146566-78-1
• Molecular Weight: 334.456
• Mol File: 146566-78-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (3S,4S,5S,6S,7S)-6-(benzyloxy)-3,5-dimethyl-4-hydroxy-7,8-(isopropylidenedioxy)oct-1-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S,5S,6S,7S)-6-(benzyloxy)-3,5-dimethyl-4-hydroxy-7,8-(isopropylidenedioxy)oct-1-ene(146566-78-1)
• EPA Substance Registry System: (3S,4S,5S,6S,7S)-6-(benzyloxy)-3,5-dimethyl-4-hydroxy-7,8-(isopropylidenedioxy)oct-1-ene(146566-78-1)

Safety Data

• Hazardous Substances Data: 146566-78-1(Hazardous Substances Data)

Upstream product

• 22323-80-4 (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 120143-04-6 (3S,4S,5S)-4-hydroxy-5,6-(isopropylidenedioxy)-3-methylhex-1-ene 
• 120143-05-7 (3S,4S,5S)-4-(benzyloxy)-5,6-(isopropylidenedioxy)-3-methylhex-1-ene 
• 74889-58-0 Methyl 3,4-O-isopropylidene-2-O-(methoxaloyl)-L-threonate 
• 114185-09-0 (2S,3R)-1,2-isopropylidenedioxy-butan-3,4-diol 
• 58650-93-4 2,3-O-bis-methyl-5,6-O-isopropylidene-L-ascorbic acid 
• 99745-86-5 (S,S)-diisopropyl tartrate (E)-crotylboronate 
• 120040-77-9 (2R,3S)-3-Benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde 
• 106357-20-4 (R,R)-diisopropyl tartrate (Z)-crotylboronate 

Downstream Products

• 120040-87-1 methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate 
• 120040-88-2 methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate 
• 120040-84-8 methyl (E,Z,E,E)-(4S,5R,6S,7S)-5-acetoxy-7-(benzyloxy)-9-bromo-14-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate 
• 120040-85-9 methyl 2β-<(E)-3-hydroxy-1-methylprop-1-enyl>-7α-acetoxy-5α-(benzyloxy)-4-bromo-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate 
• 120040-80-4 (E)-(4R,5S,6S,7S)-5-Acetoxy-7-benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4,6-trimethyl-hept-2-enoic acid methyl ester 
• 120040-82-6 methyl (E)-(4S,5R,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate 
• 120040-86-0 (1S,2S,5R,6S,7S,8R,8aR)-5-Benzyloxy-7-hydroxy-2-((E)-3-hydroxy-1-methyl-propenyl)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 146517-98-8 (E)-(4R,5S,6S,7S)-5-Acetoxy-7-benzyloxy-8,9-dihydroxy-2,4,6-trimethyl-non-2-enoic acid methyl ester 
• 146518-14-1 (1S,2S,4aS,5R,6S,7R,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-hydroxy-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 146566-81-6 methyl (E,Z,E,E)-(4S,5S,6S,7S)-5-acetoxy-7-(benzyloxy)-9-bromo-14-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate 
• 146518-03-8 (1S,2S,4aS,5S,6R,7R,8R,8aR)-7-Acetoxy-5-benzyloxy-4-bromo-2-((E)-3-hydroxy-1-methyl-propenyl)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 146518-02-7 methyl (E)-(4S,5S,6S,7S,8S)-5-acetoxy-7-(benzyloxy)-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate 
• 146608-29-9 methyl (E)-(4S,5S,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate 
• 146518-13-0 (1S,2S,4aS,5R,6S,7R,8R,8aR)-5-Benzyloxy-7-hydroxy-2-((E)-3-hydroxy-1-methyl-propenyl)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 

Relevant articles and documents

Application of the steric directing group strategy to the stereoselective synthesis of the octahydronaphthalene substructure of kijanolide and tetronolide

A highly stereoselective synthesis of the kijanolide/tetronolide octahydronaphthalene substructure 4 has been completed. The synthesis proceeds in 16 steps from L-glyceraldehyde acetonide (8), with 88% stereoselectivity and in 11% overall yield. Key steps are the following: (1) the asymmetric crotylborations of 8 and 12 that introduce the C(5), C(6), and C(8) stereocenters of 4; (2) the modified Suzuki coupling of vinylboronic acid 36 and dibromo olefin 31 that establishes the conjugated triene unit and introduces the C(9) Br steric directing group in a single operation; and (3) the highly stereoselective intramolecular Diels-Alder cycloaddition of tetraene 7. Stereochemical information obtained from the intramolecular Diels-Alder reactions of 25 and 26 provides a framework for rationalizing the role of the C(5) acetoxy group and the C(9) Br substituent on the stereoselectivity of the intramolecular Diels-Alder reaction of 7.