186885-60-9

Basic information

• Product Name: [[3-(2R,3R)-4R]-3-(3-hydroxy-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone
• Synonyms: [[3-(2R,3R)-4R]-3-(3-hydroxy-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone
• CAS NO: 186885-60-9
• Molecular Weight: 303.358
• Mol File: 186885-60-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: [[3-(2R,3R)-4R]-3-(3-hydroxy-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: [[3-(2R,3R)-4R]-3-(3-hydroxy-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone(186885-60-9)
• EPA Substance Registry System: [[3-(2R,3R)-4R]-3-(3-hydroxy-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone(186885-60-9)

Safety Data

• Hazardous Substances Data: 186885-60-9(Hazardous Substances Data)

Upstream product

• 78-85-3 2-methylpropenal 
• 101711-78-8 (3R)-3-propionyl-4-benzyloxazolidin-2-one 

Downstream Products

• 565228-87-7 [[3-(2R,3R)-4R]-3-(3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone 
• 1009561-78-7 C₂₄H₂₇NO₄ 
• 186885-64-3 (2E,4E)-(6S,7S,8S)-6,8-Dimethyl-7-triethylsilanyloxy-9-trityloxy-nona-2,4-dienoic acid ethyl ester 
• 186885-55-2 (2E,4E)-(6S,7S,8S)-7-Hydroxy-6,8-dimethyl-9-trityloxy-nona-2,4-dienoic acid ethyl ester 
• 186885-54-1 (2R,3R,4S)-2,4-Dimethyl-3-triethylsilanyloxy-5-trityloxy-pentanal 
• 186885-53-0 Triethyl-[(R)-2-methyl-1-((S)-1-methyl-2-trityloxy-ethyl)-allyloxy]-silane 
• 186885-63-2 (2S,3S,4S)-2,4-Dimethyl-3-triethylsilanyloxy-5-trityloxy-pentan-1-ol 
• 97690-88-5 (2E,4E,6S,7S,8S)-7-Hydroxy-6,8-dimethyl-9-triphenylmethoxy-2,4-nonadienoic acid 

Relevant articles and documents

Studies on the total synthesis of sanglifehrin A: Stereoselective synthesis of the C(29)-C(39) fragment

A highly stereoselective synthesis of the C(29)-C(39) fragment of the potent immunosuppressant sanglifehrin A has been accomplished by a sequence involving 16 steps (18% overall yield) from N-propionyloxazolidinone 9. Key steps are a diastereoselective hy

Stereoselectivity of model C22-23 aldol coupling for spirangiens A & B

A model system was prepared to investigate the diastereoselectivity of the key C22-23 aldol coupling for the synthesis of spirangiens A & B. The lithium enolate of model ketone 3 was coupled with the differently protected aldehydes 4 (acetonide) and 5 (silyl) giving 3:1 and 3.5:1 dr, respectively, in favour of the unnatural (S) isomer in both cases. The lack of any significant effect on the aldol stereoselectivity induced by the aldehyde protecting groups contrasts with previous literature reports.

ANALOGS OF DISCODERMOLIDE AND DICTYOSTATIN-1, INTERMEDIATES THEREFOR AND METHODS OF SYNTHESIS THEREOF

A compound of the following structure: wherein R1 is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; R2 is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; Ra, Rb and Rc are independently an alkyl group or an aryl group; Rd is an alkyl group, an aryl group, an alkoxylalkyl group, -RiSiRaRbRc or a benzyl group, wherein Ri is an alkylene group; Re is an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or -NRgRh, wherein Rg and Rh are independently H, an alkyl group or an aryl group; R3 is (CH2)n where n is and integer in the range of 0 to 5, -CH2CH(CH3)-, -CH=CH-, -CH=C(CH3)-, or -C=-C-; R4 is (CH2)p where p is an integer in the range of 4 to 12, -(CHRkl)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rsl )=C(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1 )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(RsI)CH(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRks)y5C(Rsl)=C(Rs2)CH(Rs3)CH(Rs4)-, -(CHRkI )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rsl)CH(Rs2)CH(Rs3)CH(R s4)-,wherein y1 and y2 are 1 and y3, y4 and y5 are independently 0 or 1, Rk1, Rk2, Rk3, Rk4 and Rk5 are independently H, CH3, or OR2a, and Rs1,Rs2, Rs3, and Rs4 are independently H or CH3, wherein R2a is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; and R5 is H or OR2b, wherein R2b is H, an alkyl group, an aryl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; provided that the compound is not dictyostatin 1.