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1 article(s) from Mukherjee, Mana Mohan

Synthetic avenues towards a tetrasaccharide related to Streptococcus pneumonia of serotype 6A

Aritra Chaudhury,
Mana Mohan Mukherjee and
Rina Ghosh

Beilstein J. Org. Chem. 2018, 14, 1095–1102, doi:10.3762/bjoc.14.95

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Graphical Abstract

Figure 1: The tetrasaccharides associated with the pneumonicoccal serogroup 6.

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Figure 2: Retrosynthetic analysis.

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Scheme 1: Preparation of D-glucosyl donor 6. Reaction conditions: a) NapBr/PMBCl, NaH, DMF, rt, 12 h, 90% (6a...

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Scheme 2: Preparation of L-rhamnosyl acceptor 5. Reaction conditions: a) Py, BzCl, rt, 12 h, 99%; b) DDQ, DCM...

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Scheme 3: Preparation of ribitol acceptor 7. Reaction conditions: a) Me₂C(OMe)₂, pTSA, CH₃COCH₃, rt, 81%; b) ...

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Scheme 4: Stepwise synthesis of tetrasaccharide 1. Reaction conditions: a) TMSOTf, DCM/Et₂O (5:1), 4 Å MS, −3...

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Scheme 5: One-pot synthesis of tetrasaccharide 1. Reaction conditions: a) TMSOTf, 4 Å MS, DCM/Et₂O (4:1), N₂,...

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Published 17 May 2018

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