(-)-(S)-Bromofosfamide, CBM-11-药物合成数据库

【药物名称】(-)-(S)-Bromofosfamide, CBM-11

化学结构式(Chemical Structure):

参考文献No.	50681
标题:	Process for the production of the derivs. of 1,3,2-oxazaphosphorinane
作者:	Kutner, A.; Grynkiewicz, G.; Stec, W.J.; Radzikowski, C.; Szelejeswki, W.; Kinas, R.; Misiura, K.; Grodner, J.; Kusnierczyk, H.; Pilichowska, S.
来源:	EP 0295576

合成路线图解说明: Condensation of the chiral 2-chloro-3-(alpha-methylbenzyl)tetrahydro-2H-1,3,2-oxaazaphosphorine 2-oxide (I) with 2-chloroethylamine (II) afforded the 2-(chloroethylamino) derivative (III). The chiral auxiliary group of (III) was then removed by catalytic hydrogenation with H2 over -Pd/C yielding (R)-2-(2-chloroethylamino)tetrahydro-2H-1,3,2-oxaazaphosphorine 2-oxide (IV). Acylation of (IV) with bromoacetyl bromide (V) in the presence of triethylamine hydrobromide furnished bromoacetamide (VI). The amide carbonyl group of (VI) was finally reduced by treatment with NaBH4 and BF3稥t2O.

参考文献No.	624730
标题:	(S)-(-)-Bromofosfamide (CBM-11): Synthesis and antitumor activity and cytotoxicity in mice
作者:	Misiura, K.; Kinas, R.W.; Kusnierczyk, H.; Radzikowski, C.; Stec, W.J.
来源:	Anti-Cancer Drugs 2001,12(5),453

合成路线图解说明: Condensation of the chiral 2-chloro-3-(alpha-methylbenzyl)tetrahydro-2H-1,3,2-oxaazaphosphorine 2-oxide (I) with 2-chloroethylamine (II) afforded the 2-(chloroethylamino) derivative (III). The chiral auxiliary group of (III) was then removed by catalytic hydrogenation with H2 over -Pd/C yielding (R)-2-(2-chloroethylamino)tetrahydro-2H-1,3,2-oxaazaphosphorine 2-oxide (IV). Acylation of (IV) with bromoacetyl bromide (V) in the presence of triethylamine hydrobromide furnished bromoacetamide (VI). The amide carbonyl group of (VI) was finally reduced by treatment with NaBH4 and BF3稥t2O.