Abstract
The epoxide ring of methyl 3,4-anhydro-β-d-tagatofuranoside is opened byattack of nucleophiles at C-4 to yield derivatives of D-fructose. Treatment of 2,3-O-isopropylidene-1,6-di-Op-tolylsulfonyl-β-d-fructofuranose with sulfuryl chloride resulted in attack at C-6, not C-4. 2,3-O-Isopropylidene-1,6-di-O-p-tolylsulfonyl-β-d-tagatofuranose behaved normally with this reagent. Methyl 4-deoxy-β-d-threo-hexulofuranoside was not hydrolysed by invertase.
| Original language | English |
|---|---|
| Pages (from-to) | 1-6 |
| Number of pages | 6 |
| Journal | Carbohydrate Research |
| Volume | 103 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 1 May 1982 |
Cite this
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d-fructose derivatives modified at C-4 by direct displacementand by oxirane opening. / Guthrie, R. D.; Jenkins, Ian D.; Thang, San; Watters, James J.; Yamasaki, Ryohei.
In: Carbohydrate Research, Vol. 103, No. 1, 01.05.1982, p. 1-6.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - d-fructose derivatives modified at C-4 by direct displacementand by oxirane opening
AU - Guthrie, R. D.
AU - Jenkins, Ian D.
AU - Thang, San
AU - Watters, James J.
AU - Yamasaki, Ryohei
PY - 1982/5/1
Y1 - 1982/5/1
N2 - The epoxide ring of methyl 3,4-anhydro-β-d-tagatofuranoside is opened byattack of nucleophiles at C-4 to yield derivatives of D-fructose. Treatment of 2,3-O-isopropylidene-1,6-di-Op-tolylsulfonyl-β-d-fructofuranose with sulfuryl chloride resulted in attack at C-6, not C-4. 2,3-O-Isopropylidene-1,6-di-O-p-tolylsulfonyl-β-d-tagatofuranose behaved normally with this reagent. Methyl 4-deoxy-β-d-threo-hexulofuranoside was not hydrolysed by invertase.
AB - The epoxide ring of methyl 3,4-anhydro-β-d-tagatofuranoside is opened byattack of nucleophiles at C-4 to yield derivatives of D-fructose. Treatment of 2,3-O-isopropylidene-1,6-di-Op-tolylsulfonyl-β-d-fructofuranose with sulfuryl chloride resulted in attack at C-6, not C-4. 2,3-O-Isopropylidene-1,6-di-O-p-tolylsulfonyl-β-d-tagatofuranose behaved normally with this reagent. Methyl 4-deoxy-β-d-threo-hexulofuranoside was not hydrolysed by invertase.
UR - http://www.scopus.com/inward/record.url?scp=2042490574&partnerID=8YFLogxK
U2 - 10.1016/S0008-6215(82)80002-5
DO - 10.1016/S0008-6215(82)80002-5
M3 - Article
VL - 103
SP - 1
EP - 6
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - 1
ER -