A mild and efficient method for the selective cleavage of primary p-methoxybenzyl protecting group of saccharides by Co2(CO)8–Me2PhSiH–CO system

• Published in: Tetrahedron letters Vol. 56; no. 37; pp. 5238 - 5241
• Main Authors: Qian, Peng-zhan, Yao, Wang, Huang, Lu-bai, Meng, Xiang-bao, Li, Zhong-jun
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 09.09.2015; Elsevier
• Subjects: carbohydrates; chemical reactions; chemical structure; Chemistry; Chemistry, Organic; chemoselectivity; Cleavage; Co2(CO)8; organic compounds; p-Methoxybenzyl; Physical Sciences; Regioselectivity; Science & Technology; DYKAZUPQFZQADC-CQJJOKNBSA-N; KBCUSYDBNQBFLQ-GOAGAEMWSA-N; NZFWFBXAQLIWEY-ACAPACQESA-N; AHDIGDKVLYEZIW-AXGWCIPWSA-N; KBCUSYDBNQBFLQ-KJEXFRGKSA-N; MOKYEUQDXDKNDX-OLVOQFPCSA-N; DHIOOOCUTSJGOP-CFROSVDJSA-N; NZFWFBXAQLIWEY-RVHHOKPFSA-N; Cleavage; SDKOYCMZKNAODV-XIARQSEXSA-N; FNIQKWOYSIRQMH-UHFFFAOYSA-N; QJNAQYXMYMMEGU-UHFFFAOYSA-N; XFJFPZKXGMGNEH-UHFFFAOYSA-N; FLVQOAUAIBIIGO-UHFFFAOYSA-N; Regioselectivity; VZNQRGUOZOHZJJ-FSKRBKRMSA-N; QDBFCZCIBRFQBR-UHFFFAOYSA-N; SXRAMPOIZZIYLG-SMGOGFSKSA-N; VZNQRGUOZOHZJJ-YXPDNQQPSA-N; AUWDOZOUJWEPBA-UHFFFAOYSA-N; XQXPZJNPTLMVNJ-COVCTBSSSA-N; MVEWWBQAFXHEGS-VMYVWREKSA-N; KWMNAYQBQGSFPV-WBFXSEPVSA-N; PKCVTFSSBWEPPW-UHFFFAOYSA-N; AVEHENYSRYRUHC-UHFFFAOYSA-N; NZFWFBXAQLIWEY-GOAGAEMWSA-N; OWZUZKXGKZBEKT-FMQWCNCSSA-N; SXRAMPOIZZIYLG-ASIXIOGKSA-N; NZFWFBXAQLIWEY-XHTBTGSUSA-N; p-Methoxybenzyl; WGBBKMOBGARXLF-UHFFFAOYSA-N; KBCUSYDBNQBFLQ-RVHHOKPFSA-N; Co2(CO)8; MVEWWBQAFXHEGS-YTEOULKDSA-N; VZNQRGUOZOHZJJ-KYZDGCSASA-N; VZNQRGUOZOHZJJ-YTEOULKDSA-N; DHIOOOCUTSJGOP-HVIIUBQOSA-N; MVEWWBQAFXHEGS-YXPDNQQPSA-N; ETHERS; DEPROTECTION; Co-2(CO)
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2015.07.051

[Display omitted] A mild and efficient method to selectively cleave p-methoxybenzyl (PMB) ether with a catalytic amount of Co2(CO)8, hydrosilane and CO (1atm) is presented. The cleavage reaction shows regioselectivity to primary O-PMB of a variety of permethoxybenzylated saccharides and chemoselectivity to O-Bn, sulfur-containing group and common ester protecting groups.