Gulopyranoside, methyl 2,3-anhydro

With sodium hydroxide, methyl 2,3-anhydro-a-D-allopyranoside yields methyl 3,6-anhydro-a-D-glucopyranoside by intramolecular attack on the epoxide ring by the 6-hydroxyl group.72 Methyl 2,3-anhydro-a-D-gulopyranoside behaves similarly, and its intermediacy accounts for the conversion of methyl 3,4-anhydro-a-D-galactopyrano-side into methyl 3,6-anhydro-a-D-galactopyranoside on treatment with alkali.67... 

Neighboring-group participation by the vicinal, trans-acetoxyl group (see p. 125) serves to explain the abnormal behavior of methyl 4-0-acetyl-2,3-anhydro-6-0-benzyl- or -trityl-a-D-gulopyranoside with hydrogen chloride in acetone, or with 80% aqueous acetic acid, which give D-galactose, instead of the D-idose, derivatives.67 In the same way, 2-0-acetyl-3,4-anhydro-D-altropyranosides yield D-man-nosides, not D-idosides.9 6z(see p. 125). 

J. L. Frahn, Preparation of the 2,3-anhydro-4,6-0-benzylidene derivatives of methyl a- and /J-D-talopyranoside and of methyl a-D-gulopyranoside, Aust. J. Chem., 33 (1980) 1021-1024. 

Methyl 2,3-anhydro-4,6-0-benzylidene-a-D-gulopyranoside HCl 2-substituted D-idose a 49... 

Me glycoside, 4-Ac Methyl 4-0-acetyl-2,3-anhydro-6-deoxy-a-D-gulopyranoside [6893-97-6]... 

Me glycoside, 6-tosyl Methyl 2,3-anhydro-6-O-tosyl-a-D-gulopyranoside Mp 60-62°. Md +24.7 (CHCI3). 

Me glycoside, 6-trityl Methyl 2,3-anhydro-6-O-trityl-a-D-gulopyranoside [5592-12-1]... 

Benzyl 2,3-anhydro-4-0-a-L-arabinopyranosyl-p-D-ribopyranoside, A-848 Benzyl 2,3-anhydro-4,6-0-benzylidene-a-D-allopyranoside, A-484 Benzyl 2,3-anhydro-4,6-0-benzylidene-p-D-gulopyranoside, A-639 Benzyl 2,3-anhydro-4,6-0-benzylidene-a-D-mannopyranoside, A-676 Benzyl 3,4-anhydro-2,6-dideoxy-a-L-r -hexopyranoside, A-591 Benzyl 2,3-anhydro-4- O - p-D-galactopyranosyl- p-D-ribopyranoside, G-173 Benzyl 2,3-anhydro-a-D-mannopyranoside, A-676 Benzyl 2,3-anhydro-p-D-mannopyranoside, A-676 Benzyl 3,4-anhydro-2-0-mesyl-6-0-trityl-a-D-altropyranoside, A-495 Benzyl 2,3-anhydro-4-0-methyl-p-D-ribopyranoside, A-693 Benzyl 2,3-anhydro-p-D-ery /iro-pentopyranosid-4-ulose, A-682 Benzyl 2,3-anhydro-p-L-eyy /iro-pentopyranosid-4-ulose, A-682 Benzyl 2,3-anhydro-a-D-ribopyranoside, A-693 Benzyl 2,3-anhydro-p-D-ribopyranoside, A-693 Benzyl 2,3-anhydro-p-L-ribopyranoside, A-693... 

Methyl 2-0-acetyl-3,4-anhydro-a-D-arabinopyranoside, A-504 Methyl 2-0-acetyl-3,4-anhydro-p-L-arabinopyranoside, A-504 Methyl 4-0-acetyl-2,3-anhydro-6-deoxy-a-D-gulopyranoside, A-527 Methyl 4-0-acetyl-2,3-anhydro-6-deoxy-p-D-gulopyranoside, A-527 Methyl 4-0-acetyl-2,3-anhydro-6-deoxy-a-D-mannopyranoside, A-687 Methyl 4-0-acetyl-3,6-anhydro-a-D-galactopyranoside, A-620 Methyl 5-0-acetyl-2,3-anhydro-a-D-lyxofuranoside, A-664 Methyl 5-0-acetyl-2,3-anhydro-p-D-lyxofuranoside, A-664 Methyl 3-0-acetyl-2,6-anhydro-4-0-methyl-p-D-mannopyranoside, A-678 Methyl 4-0-acetyl-2,3-anhydro-a-D-rhamnopyranoside, A-687 Methyl 5-0-acetyl-2,3-anhydro-a-D-ribofuranoside, A-690 Methyl 5-0-acetyl-2,3-anhydro-p-D-ribofuranoside, A-690 Methyl 4-0-acetyl-2,3-anhydro-p-D-ribopyranoside, A-693 Methyl 4-0-acetyl-2,3-anhydro-6-0-trityl-a-D-mannopyranoside, A-676 Methyl 2-0-acetyl-p-L-arabinopyranoside, M-153 Methyl 3-0 -acetyl-2-azido-4,6-0 -benzylidene-2-deoxy-a-D-mannopyranoside, A-912... 

Methyl 2,3-anhydro-4-bromo-4-deoxy-a-L-lyxopyranoside, B-84 Methyl 2,3-anhydro-4-bromo-4-deoxy-6- O -trityl-a-D-gulopyranoside, B-78 Methyl 2,3-anhydro-4-chloro-4-deoxy-a-L-xylopyranoside, C-110 Methyl 2,3-anhydro-6-deoxy-a-D-allopyranoside, A-516 Methyl 2,3-anhydro-6-deoxy-a-L-allopyranoside, A-516 Methyl 3,6-anhydro-2-deoxy-4,5 7,8-di-0-isopropylidene-D-g-/ycer(3-D-ia/o-octonate, M-174... 

Methyl 2,3-anhydro-6-0-trityl-a-D-allopyranoside, A-484 Methyl 3,4-anhydro-6-0-trityl-a-D-altropyranoside, A-495 Methyl 2,3-anhydro-6-0-trityl-a-D-gulopyranoside, A-639 Methyl 2,3-anhydro-5-0-trityl-a-D-lyxofuranoside, A-664 Methyl 2,3-anhydro-5-0-trityl-p-D-lyxofnranoside, A-664 Methyl 2,3-anhydro-6-0-trityl-a-D-mannopyranoside, A-676 Methyl 2,3-anhydro-5-0-trityl-a-D-ribofnranoside, A-690 Methyl 2,3-anhydro-5-0-trityl-p-D-ribofnranoside, A-690 Methyl 3,5-anhydro-p-D-xylofuranoside, A-728 Methyl p-D-apiofuranosyl-(l ->6)-p-D-glucopyranoside, A-784 Methyl arabinofuranoside, M-152... 

Methyl 4-0-acetyl-2,3-anhydro-6-deoxy-a-D-gulopyranoside, A-521 Methyl 4-0-acetyl-2,3-anhydro-6-deoxy-p-D-gulopyranoside, ASH Methyl 3-0-acetyl-6-deoxy-a-D-gulopyranoside, D-146 Methyl 4-0 -acety l-6-deoxy-2,3-0 -isopropylidene-a-D-gulopy ranoside, D-146... 

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