956 CHAPTER 22 Carbohydrates
- Enolization (Section 22.5).
- Osazone formation (Section 22.6).
- Chain elongation: the Kiliani–Fischer synthesis (Section 22.7).
- Chain shortening: the Ruff degradation (Section 22.8).
- Acylation (Section 22.12).
- Alkylation (Section 22.12).
- Acetal (and ketal) formation (Section 22.13).
HCl
ROH
OHCH 2 OH
HO
HO
OHO
ORCH 2 OH
HO
HO
OHOORCH 2 OH
HO
HO
OHO
+OHCH 2 OHOHO
HOHO
OCH 3CH 2 OCH 3OCH 3O
CH 3 OCH 3 OCH 3 I
excess
Ag 2 OOHCH 2 OHOHO
HOHO
OCCH 3CH 2 OCCH 3OCCH 3O
CH 3 COCH 3 COCH 3 COCCH 3
excess
pyridineOOOOOOO+ CO 2- Ca(OH) 2
(CHOH)n 3. H 2 O 2 , Fe 3 +
CH 2 OHHC O(CHOH)n − 1CH 2 OH- Br 2 , H 2 O HC O
2. H 2 , Pd/BaSO 4
(CHOH)n 3. H 3 O+
CH 2 OHHC O(CHOH)n + 1CH 2 OH- NaC N/HCl HC O
+ 3 NH 2 NH(CHOH)nCHOHCH 2 OHHC O++(CHOH)nCCH 2 OHHC NNHC 6 H 5NNHC 6 H 5 NH 3 + 2 H 2 ONH 2
catalytic
H+HO−
H 2 O (CHOH)nCHOHCH 2 OHHC O(CHOH)nCH 2 OHCOCH 2 OH(CHOH)nCH 2 OHCOHHC OHH 2 O
HO−