Reaction of D-ribo-hexos-3-ulose and of 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexo-1,4-furanos-3-ulose 3-hydrate with methanol-hydrogen chloride. A preparation of D-ribo-3-hexulose
1
Chemistry Department, Swedish Forest Products Research Laboratory, Box 5604, S-114 86 Stockholm Sweden
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Publication type: Journal Article
Publication date: 1971-02-01
scimago Q3
wos Q2
SJR: 0.423
CiteScore: 4.0
Impact factor: 2.5
ISSN: 00086215, 1873426X
Organic Chemistry
Biochemistry
General Medicine
Analytical Chemistry
Abstract
The reaction of D - ribo -hexos-3-ulose ( 1 ) with methanol-hydrogen chloride yielded as major products methyl (methyl β- D - ribo -hexo-1,4-furanosid)-β- D -3-ulo-3,6-furanoside ( 4 ), and methyl (methyl α- D - ribo -hexo-1,4-furanosid)-β- D -3-ulo-3,6-furanoside ( 5 ). Similar treatment of 1,2:5,6-di- O -isopropylidene-α- D - ribo -hexo-1,4-furanos-3-ulose 3-hydrate ( 2 ) afforded 4 and 5 together with methyl (1,2- O -isopropylidene-α- D - ribo -hexo-1,4-furanos)-β- D -3-ulo-3,6-furanoside ( 3 ). Compounds 3, 4, and 5 were all partially hydrolyzed to methyl α, β- D - ribo -hexo-1,4-furanos-β- D -3-ulo-3,6-furanoside ( 6 ). Catalytic hydrogenation of 6 gave methyl β- D - ribo -3-hexulo-3,6-furanoside ( 7 ), which was hydrolyzed to D - ribo -3-hexulose ( 8 ). The preparation of 8 by partial reduction of 1 does not appear to be practicable.
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Humphries H. P., Theander O. Reaction of D-ribo-hexos-3-ulose and of 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexo-1,4-furanos-3-ulose 3-hydrate with methanol-hydrogen chloride. A preparation of D-ribo-3-hexulose // Carbohydrate Research. 1971. Vol. 16. No. 2. pp. 317-325.
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Humphries H. P., Theander O. Reaction of D-ribo-hexos-3-ulose and of 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexo-1,4-furanos-3-ulose 3-hydrate with methanol-hydrogen chloride. A preparation of D-ribo-3-hexulose // Carbohydrate Research. 1971. Vol. 16. No. 2. pp. 317-325.
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RIS
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TY - JOUR
DO - 10.1016/s0008-6215(00)81167-2
UR - https://doi.org/10.1016/s0008-6215(00)81167-2
TI - Reaction of D-ribo-hexos-3-ulose and of 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexo-1,4-furanos-3-ulose 3-hydrate with methanol-hydrogen chloride. A preparation of D-ribo-3-hexulose
T2 - Carbohydrate Research
AU - Humphries, H P
AU - Theander, O.
PY - 1971
DA - 1971/02/01
PB - Elsevier
SP - 317-325
IS - 2
VL - 16
SN - 0008-6215
SN - 1873-426X
ER -
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BibTex (up to 50 authors)
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@article{1971_Humphries,
author = {H P Humphries and O. Theander},
title = {Reaction of D-ribo-hexos-3-ulose and of 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexo-1,4-furanos-3-ulose 3-hydrate with methanol-hydrogen chloride. A preparation of D-ribo-3-hexulose},
journal = {Carbohydrate Research},
year = {1971},
volume = {16},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/s0008-6215(00)81167-2},
number = {2},
pages = {317--325},
doi = {10.1016/s0008-6215(00)81167-2}
}
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MLA
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Humphries, H. P., and O. Theander. “Reaction of D-ribo-hexos-3-ulose and of 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexo-1,4-furanos-3-ulose 3-hydrate with methanol-hydrogen chloride. A preparation of D-ribo-3-hexulose.” Carbohydrate Research, vol. 16, no. 2, Feb. 1971, pp. 317-325. https://doi.org/10.1016/s0008-6215(00)81167-2.