(1R,10R,11S)-6-Bromo-11-[[tert-butyl(diphenyl)silyl]oxy]-6-methyl-8,13-dioxa-2,4-diazatricyclo[8.2.1.0(2,7)]tridecane-3,5-dione -Drug Synthesis Database

【结构式】

【分子编号】12243

【品名】(1R,10R,11S)-6-Bromo-11-[[tert-butyl(diphenyl)silyl]oxy]-6-methyl-8,13-dioxa-2,4-diazatricyclo[8.2.1.0(2,7)]tridecane-3,5-dione

【CA登记号】

【分子式】C₂₆H₃₁BrN₂O₅Si

【分子量】559.53212

【元素组成】C 55.81% H 5.58% Br 14.28% N 5.01% O 14.3% Si 5.02%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IV)

A new synthesis of stavudine has been reported: The condensation of thymine (I) with methyl 2-deoxyribofuranoside (II) by means of N-bromosuccinimide (NBS) followed by protection with TBDPS-Cl gives the intermediate (III), which is cyclized by means of trimethylsilyl triflate (TMS-OTf), yielding the cyclothymidine derivative (IV). The deprotection of (IV) with tetrabutylammonium fluoride affords the unprotected compound (V), which is finally treated successively with triflate anhydride, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and Zn/acetic acid. The unprotected intermediate compound (V) can also be obtained by cyclization of thymidine (VI) by means of NBS in DMF, catalyzed by trifluoroacetic acid.

参考文献中间体

合成目标

【1】 Lowe, R.F.; Lipshutz, B.H.; Stevens, K.L.; A novel route to the anti-HIV nucleoside d4T. Tetrahedron Lett 1995, 36, 16, 2711.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	12204	5-Methyl-2,4(1H,3H)-pyrimidinedione; Thymine	65-71-4	C₅H₆N₂O₂	详情	详情
(II)	12241	(2R,3S)-2-(Hydroxymethyl)-5-methoxytetrahydro-3-furanol		C₆H₁₂O₄	详情	详情
(III)	12242	5-Bromo-6-[((2R,3S)-3-[[tert-butyl(diphenyl)silyl]oxy]-5-methoxytetrahydro-2-furanyl)methoxy]-5-methyldihydro-2,4(1H,3H)-pyrimidinedione		C₂₇H₃₅BrN₂O₆Si	详情	详情
(IV)	12243	(1R,10R,11S)-6-Bromo-11-[[tert-butyl(diphenyl)silyl]oxy]-6-methyl-8,13-dioxa-2,4-diazatricyclo[8.2.1.0(2,7)]tridecane-3,5-dione		C₂₆H₃₁BrN₂O₅Si	详情	详情
(V)	12244	(1R,10R,11S)-6-Bromo-11-hydroxy-6-methyl-8,13-dioxa-2,4-diazatricyclo[8.2.1.0(2,7)]tridecane-3,5-dione		C₁₀H₁₃BrN₂O₅	详情	详情
(VI)	12161	Thymidine; 1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione	50-89-5	C₁₀H₁₄N₂O₅	详情	详情

Extended Information