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Allyl 2-O-acetyl-3-O-benzyl-α-L-rhamnopyranoside - CAS 940274-20-4

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Category
Main Product
Product Name
Allyl 2-O-acetyl-3-O-benzyl-α-L-rhamnopyranoside
Catalog Number
940274-20-4
Synonyms
Allyl 2-O-acetyl-3-O-benzyl-a-L-rhamnopyranoside;Allyl 2-O-acetyl-3-O-benzyl-alpha-L-rhamnopyranoside
CAS Number
940274-20-4
Molecular Weight
336.38
Molecular Formula
C18H24O6
COA
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MSDS
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Structure
CAS 940274-20-4 Allyl 2-O-acetyl-3-O-benzyl-α-L-rhamnopyranoside
Specification
Purity
95%
Reference Reading
1.Efficient synthesis of building blocks for branched rhamnogalacturonan I fragments.
Pogosyan A1, Gottwald A, Michalik D, Endress HU, Vogel C. Carbohydr Res. 2013 Oct 18;380:9-15. doi: 10.1016/j.carres.2013.06.019. Epub 2013 Jun 28.
Starting from allyl 2-O-acetyl-3-O-benzyl-α-l-rhamnopyranoside (3), allyl (2,3,4,6-tetra-O-benzoyl-β-d-galactopyranosyl)-(1→4)-2-O-acetyl-3-O-benzyl-α-l-rhamnopyranoside (5) was synthesized under Helferich conditions. Module 5 was converted to 2,3,4,6-tetra-O-benzoyl-β-d-galactopyranosyl-(1→4)-2-O-acetyl-3-O-benzyl-α-l-rhamnopyranosyl bromide (8) which was then coupled with methyl (allyl 2,3-di-O-benzyl-β-d-galactopyranosid)uronate (11) to provide methyl (2,3,4,6-tetra-O-benzoyl-β-d-galactopyranosyl)-(1→4)-(2-O-acetyl-3-O-benzyl-α-l-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-d-galactopyranosid)uronate (14). Alternatively, module 5 was transformed into allyl 2,3,4,6-tetra-O-benzoyl-β-d-galactopyranosyl-(1→4)-3-O-benzyl-α-l-rhamnopyranoside (9) suitable as an acceptor for the glycosylation with methyl 4-O-acetyl-2,3-di-O-benzyl-α/β-d-galactopyranosyluronate N-phenyl trifluoroacetimidate (13) to yield allyl (methyl 4-O-acetyl-2,3-di-O-benzyl-α-d-galactopyranosyluronate)-(1→2)-[2,3,4,6-tetra-O-benzoyl-β-d-galactopyranosyl]-(1→4)-3-O-benzyl-α-l-rhamnopyranoside (15).
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