Benzyl Chloromethyl Ether

Connor, D. S.; Klein, Gerald W.; Taylor, Graeme K.; Boeckman, Robert K.; Medwid, James

doi:10.1002/0471264180.os052.04

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(3s6r)-3-[n 6 -(Benzyloxycarbonyl)adenin-9-yl]-6-tert-butoxy...1

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Cited by 10 publications

(12 citation statements)

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“…A small sample was removed after 2 min for TLC and acidified. TLC (CHCl 3 -MeOH-HOAc 85 : 10 : 5), R f 0.36 (product) and 0.74 (10). After 45 min H 2 O (1 ml) was added and the THF was evaporated off.…”

Section: (3s6r)-3-[n 6 -(Benzyloxycarbonyl)adenin-9-yl]-6-tert-butoxy...mentioning

confidence: 99%

Synthesis of (3R,6R)- and (3S,6R)-piperidinone PNA

Püschl

Boesen

Tedeschi

et al. 2001

J. Chem. Soc., Perkin Trans. 1

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Section: (3s6r)-3-[n 6 -(Benzyloxycarbonyl)adenin-9-yl]-6-tert-butoxy...mentioning

confidence: 99%

Synthesis of (3R,6R)- and (3S,6R)-piperidinone PNA

Püschl

Boesen

Tedeschi

et al. 2001

J. Chem. Soc., Perkin Trans. 1

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“…Benzyloxymethyl (BOM) group has been utilized as a convenient protecting group for the uridine ureido nitrogen (P 1 ). 5 However, we and other groups observed that BOM deprotection of uridine derivatives under hydrogenation conditions often resulted in poor yield with over-reduction product(s). 6 In general, hydrogenolytic deprotection is the only method to remove the BOM group of the uridine ureido nitrogen.…”

Section: Introductionmentioning

confidence: 78%

A new protecting group and linker for uridine ureido nitrogen

Wang

Kurosu

2012

Tetrahedron

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(2,6-Dichloro-4-methoxyphenyl) (2,4,6-trichlorophenyl) methoxymethyl chloride [1, monomethoxydiphenylmethoxylmethyl chloroide (MDPM-Cl)] shows a significant relative stability and 1 reacts with uridine ureido nitrogen in the presence of DBU to form the corresponding protected uridine 8 in 95% yield. The MDPM-protected uridines are stable to a wide variety of conditions utilized for the synthesis of analogs of capuramycin and muraymycins. Significantly, the MDPM protecting group can conveniently be deprotected by using 30% TFA in CH2Cl2. In addition, polymer-bound MDPM-Cl 23 is useful for immobilization of uridine derivatives.

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“…1-(Methoxycarbonylmethyl)thymine, 37 benzyloxymethyl chloride, 41 2-phenyl-1,3-dioxan-5-one monohydrate (32), 35 and 1,1-bis(benzyloxymethyl)ethylene (43), 23 were prepared according to literature procedures. NaH was ca.…”

Section: Methodsmentioning

confidence: 99%