101906-21-2

Basic information

• Product Name: [(2R,4R,6R,8R,9S)-2-((E)-(R)-6-Benzyloxy-3,5-dimethyl-hex-2-enyl)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-dimethyl-silane
• Synonyms: [(2R,4R,6R,8R,9S)-2-((E)-(R)-6-Benzyloxy-3,5-dimethyl-hex-2-enyl)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-dimethyl-silane
• CAS NO: 101906-21-2
• Molecular Weight: 530.864
• Mol File: 101906-21-2.mol

Chemical Properties

• CAS DataBase Reference: [(2R,4R,6R,8R,9S)-2-((E)-(R)-6-Benzyloxy-3,5-dimethyl-hex-2-enyl)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-dimethyl-silane(CAS DataBase Reference)
• NIST Chemistry Reference: [(2R,4R,6R,8R,9S)-2-((E)-(R)-6-Benzyloxy-3,5-dimethyl-hex-2-enyl)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-dimethyl-silane(101906-21-2)
• EPA Substance Registry System: [(2R,4R,6R,8R,9S)-2-((E)-(R)-6-Benzyloxy-3,5-dimethyl-hex-2-enyl)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-dimethyl-silane(101906-21-2)

Safety Data

• Hazardous Substances Data: 101906-21-2(Hazardous Substances Data)

Upstream product

• 101906-32-5 (2S,4S,6S,8R,9S)-2-<(5R)-(2E)-6-Benzyloxy-3,5-dimethyl-2-hexen-1-yl>-8,9-dimethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecane 
• 132180-07-5 (E)-(3R,8R)-9-Benzyloxy-6,8-dimethyl-3-(tetrahydro-pyran-2-yloxy)-non-5-enal 
• 132180-06-4 (5S,6R)-5-Methyl-6-(tetrahydro-pyran-2-yloxy)-heptan-2-one 
• 101977-99-5 (4S)-4-<(2S,7R)-(4E)-8-benzyloxy-2-hydroxy-5,7-dimethyloct-4-en-1-yl>-2,2-dimethyl-1,3-dioxolane 
• 114092-35-2 2-<(3S,4R)-3-methyl-4-p-nitrobenzoyloxypentyl>-1,3-dioxolane 
• 92175-21-8 [1-((2R,6S,8R,9S)-8,9-Dimethyl-1,5,7-trioxa-spiro[5.5]undec-2-ylmethyl)-vinyloxy]-trimethyl-silane 
• 101977-90-6 (2R,6R,8R,9S)-8,9-dimethyl-2-(2-oxopropyl)-1,5,7-trioxaspiro<5.5>undecane 
• 101977-89-3 (2R,6R,8R,9S)-2-(2-methylallyl)-8,9-dimethyl-1,5,7-trioxaspiro<5.5>undecane 
• 101977-98-4 (S)-2,2-dimethyl-4-((S)-oxiran-2-ylmethyl)-1,3-dioxolane 
• 100-39-0 benzyl bromide 
• 101906-25-6 (2R)-benzyl-(2-methylpent-4-ynyl) ether 
• 104265-23-8 (2R,S)-((2S)-3-benzyloxy-2-methylpropoxy)tetrahydropyran 
• 63930-50-7 (S)-(+)-3-benzyloxy-2-methylpropyl bromide 
• 63930-49-4 (R)-3-(benzyloxy)-2-methylpropan-1-ol 

Downstream Products

• 82045-55-4 (2S,4S,6S,8R,9S)-4-(dimethyl-t-butylsiloxy)-2-<(5R,2E,6E,8E)-9-(5-methoxycarbonyl-p-tolyl)-3,5dimethyldeca-2,6,8-trienyl>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane 
• 82045-55-4 (2S,4S,6S,8R,9S)-4-(dimethyl-t-butylsiloxy)-2-<(5R,2E,6Z,8E)-9-(5-methoxycarbonyl-p-tolyl)-3,5dimethyldeca-2,6,8-trienyl>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane 
• 114125-40-5 2-{(1E,7E)-(R)-3-Benzenesulfonyl-4-benzoyloxy-9-[(2R,4S,6R,8R,9S)-4-(tert-butyl-dimethyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-1,5,7-trimethyl-nona-1,7-dienyl}-4-methoxy-5-methyl-benzoic acid methyl ester 
• 114092-33-0 2-{(1E,7E)-(R)-9-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-dimethyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4-methanesulfonyloxy-1,5,7-trimethyl-nona-1,7-dienyl}-4-methoxy-5-methyl-benzoic acid methyl ester 
• 114092-32-9 2-{(1E,7E)-(R)-9-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-dimethyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4-hydroxy-1,5,7-trimethyl-nona-1,7-dienyl}-4-methoxy-5-methyl-benzoic acid methyl ester 
• 82045-55-4 (2S,4S,6S,8R,9S)-4-(dimethyl-t-butylsiloxy)-2-<(5R,2E,6E/Z,8E)-9-(5-methoxycarbonyl-p-tolyl)-3,5dimethyldeca-2,6,8-trienyl>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane 
• 82045-56-5 2-[(1E,3E,7E)-(R)-9-((2R,4S,6R,8R,9S)-4-Hydroxy-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-1,5,7-trimethyl-nona-1,3,7-trienyl]-4-methoxy-5-methyl-benzoic acid methyl ester 

Relevant articles and documents

A NEW APPROACH TO 1,7-DIOXASPIROUNDEC-4-ENES VIA METALLATED ALLENOL ETHERS. SYNTHESIS OF LACRIMIN A.

Key steps in the first total synthesis of Lacrimin A (2) include (a) the use of methoxyallene as an enone-1,3-dianion equivalent; (b) the use of a new copper-catalysed migratory insertion reaction to construct a tri-substituted alkene stereoselectively; and (c) the use of a Pd(0)-catalysed coupling reaction to generate an isochromanone ring.

A SYNTHESIS OF LACRIMIN A

A convergent synthesis of Lacrimin A (2) is described in which a Wadsworth-Emmons reaction was used to constract the C10-C11 double bond and link the isochroman-1-one phosphonate (4) to the spiroacetal aldehyde (3).

The 3,4-Dihydro-2H-pyran Approach to (+)-Milbemycin β3. Part 2. An Improved Synthesis of (2R,4S,6S,8R,9S)-2--8,9-dimethyl-4-(dimethyl-t-butylsilyloxy)-1,7-dioxaspiroundecane

A more efficient synthesis of the title compound (2), previously used in a total synthesis of (+)-milbemycin β3 (1), is described.The key step in the sequence involves a nucleophilic cleavage of the oxirane (4) by the organocuprate derived from

A Directed Aldol Approach to (+)-Milbemycin β3

Key steps in a total synthesis of (+)-milbemycin β3 are the construction of the 1,7-dioxaspiroundecane (10) by a Lewis acid-catalysed intramolecular directed aldol reaction and the use of sulphone-based olefination reactions for the constr

A Synthesis of (+)-Milbemycin β3. The Directed Aldol Approach

A synthesis of (+)-milbemycin β3, is reported in which key steps are the construction of the 1,7-dioxaspiroundecane (15) by a Lewis acid-catalysed intramolecular directed aldol reaction and the use of sulphone-based olefination reactions f