201275-55-0

Basic information

• Product Name: (S)-4-(4-bromobenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane
• Synonyms: (S)-4-(4-bromobenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane
• CAS NO: 201275-55-0
• Molecular Weight: 301.18
• Mol File: 201275-55-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-4-(4-bromobenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-(4-bromobenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane(201275-55-0)
• EPA Substance Registry System: (S)-4-(4-bromobenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane(201275-55-0)

Safety Data

• Hazardous Substances Data: 201275-55-0(Hazardous Substances Data)

Upstream product

• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 589-15-1 1-bromomethyl-4-bromobenzene 

Downstream Products

• 1313715-38-6 (R)-3-[4-(furan-2-yl)benzyloxy]propane-1,2-diol 
• 1313715-60-4 C₂₃H₂₇N₃O₈ 
• 1313715-58-0 C₂₃H₂₉N₃O₉ 
• 1313715-57-9 C₂₆H₃₃N₃O₉ 
• 1313715-47-7 diisopropylamidophosphorous acid (S)-2-[bis(4-methoxyphenyl)(phenyl)methoxy]-1-[4-(furan-2-yl)benzyloxymethyl]ethyl ester 2-cyanoethyl ester 
• 1313715-45-5 (S)-1-[bis(4-methoxyphenyl)(phenyl)methoxy]-3-[4-(furan-2-yl)benzyloxy]propan-2-ol 
• 1313715-43-3 (S)-4-[4-(furan-2-yl)benzyloxymethyl]-2,2-dimethyl-1,3-dioxolane 
• 201275-50-5 (2R,4S,6S,8S,10S)-2-Benzyloxymethyl-8-hydroxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undecan-4-ol 
• 201275-49-2 (2R,4S,6R,8S,10S)-2-Benzyloxymethyl-8-hydroxymethyl-10-methoxy-1,7-dioxa-spiro[5.5]undecan-4-ol 
• 201275-41-4 (S)-4-((S)-3-{2-[(2S,4R)-5-Benzyloxy-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentyl]-[1,3]dithian-2-yl}-2-methoxy-propyl)-2,2-dimethyl-[1,3]dioxolane 
• 201275-45-8 Carbonic acid (R)-1-(4-bromo-benzyloxymethyl)-but-3-enyl ester tert-butyl ester 
• 201275-56-1 [(R)-1-(4-Bromo-benzyloxymethyl)-2-(S)-oxiranyl-ethoxy]-tert-butyl-dimethyl-silane 
• 201275-46-9 (4R,6S)-4-(4-Bromo-benzyloxymethyl)-6-iodomethyl-[1,3]dioxan-2-one 
• 201275-42-5 ((R)-1-Benzyloxymethyl-2-(S)-oxiranyl-ethoxy)-tert-butyl-dimethyl-silane 

Relevant articles and documents

Spongistatin synthetic studies. 2. Assembly of the C(18-28) spiroketal

The C(18-28) CD-ring spiroketal subunit of the spongistatins, marine polyether macrolides with unprecedented antitumor activity, has been generated via a highly convergent and completely stereocontrolled sequence. Key operations include a one-flask dithiane bisalkylation and a metal-assisted spiroketal equilibration.

Spongipyran synthetic studies. Total synthesis of (+)-spongistatin 2

Evolution of a convergent synthetic strategy to access (+)-spongistatin 2 (2), a potent cytotoxic marine macrolide, is described. Highlights of the synthesis include: development of a multicomponent dithiane-mediated linchpin union tactic, devised and implemented specifically for construction of the spongistatin AB and CD spiro ring systems; application of a CaII ion controlled acid promoted equilibration to set the thermodynamically less stable axial-equatorial stereogenicity in the CD spiroketal; use of sulfone addition/Julia methylenation sequences to unite the AB and CD fragments and introduce the C(44)-C(51) side chain; and fragment union and final elaboration to (+)-spongistatin 2 (2) exploiting Wittig olefination to unite the advanced ABCD and EF fragments, followed by regioselective Yamaguchi macrolactonization and global deprotection. Correction of the CD spiro ring stereogenicity was subsequently achieved via acid equilibration in the presence of CaII ion to furnish (+)-spongistatin 2 (2). The synthesis proceeded with a longest linear sequence of 41 steps.