Synthesis of Trisaccharide of Incanoside from Caryopteris incana

Article abstract of DOI:10.1081/SCC-120027292

Trisaccharide phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1 → 2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1 → 3)-2-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside, the sugar core of incanosides from Caryopteris incana (T_HUNB.), was syn

Full text of DOI:10.1081/SCC-120027292

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Synthesis of Trisaccharide of Incanoside from
Caryopteris incana
Jubiao Li a & Yanguang Wang a
a Department of Chemistry , Zhejiang University , Hangzhou, 310027, P. R. China
Published online: 16 Aug 2006.
To cite this article: Jubiao Li & Yanguang Wang (2004) Synthesis of Trisaccharide of Incanoside from Caryopteris incana ,
Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry, 34:3,
515-522, DOI: 10.1081/SCC-120027292
To link to this article: http://dx.doi.org/10.1081/SCC-120027292
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SYNTHETIC COMMUNICATIONSw
Vol. 34, No. 3, pp. 515–522, 2004
Synthesis of Trisaccharide of Incanoside
from Caryopteris incana
*
Jubiao Li and Yanguang Wang
Department of Chemistry, Zhejiang University, Hangzhou, P. R. China
ABSTRACT
Trisaccharide phenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl-(1 ! 2)-
3,4-di-O-benzoyl-a-L-rhamnopyranosyl-(1 ! 3)-2-O-acetyl-4,6-O-ben-
zylidene-1-thio-b-D-glucopyranoside, the sugar core of incanosides from
Caryopteris incana (THUNB.), was synthesized via a concise route. The key
step of this route involved the preparation of decisive disaccharide
acceptor from the phenyl 2-acetyl-3,4-di-O-benzoyl-a-L-rhamnopyrano-
syl-(1 ! 3)-2-O-acetyl-4,6-O-benzylidene-1-thio-b-D-glucopyranoside
by regioselective and chemoselective deacetylation method.
Key Words: Trisaccharide; Incanoside; Caryopteris incana; Synthesis.
In recent years, evidence has accumulated suggesting that free radicals
are involved in many deterioration processes. They attack the unsaturated fatty
*
Correspondence: Yanguang Wang, Department of Chemistry, Zhejiang University,
Hangzhou 310027, P. R. China.
515
DOI: 10.1081/SCC-120027292
0039-7911 (Print); 1532-2432 (Online)
www.dekker.com
Copyright # 2004 by Marcel Dekker, Inc.

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acids in the biomembranes resulting in membrane lipid peroxidation, which is
strongly connected with aging, carcinogenesis and atherosclerosis.[1,2] It was
also reported that many diseases of fruits and vegetables, including cancer and
cardio- and cerebrovascular diseases, were ascribed to the oxidation resulting
from the active oxygen molecules. Free radicals also attack DNA and cause
mutation leading to cancer.[3] Thus it is desirable to look for effective radical
scavengers.
In 1999, Janjun Gao et al.[4] isolated incanoside C, D and E (Fig. 1) from
the whole plant of Caryopteris incana (THUNB.) which was proved to exhibit
good radical scavenging activities against DPPH radical and inhibitory actives
against the oxidation of linoleic acid.[5] Here, for the first time we report the
synthesis of trisaccharide of incanosides C, D and E.
Although the linear trisaccharide structure is not very complex, the high
stereoselective and regioselective coupling for the construction of b(1 ! 2)
and a(1 ! 3) linkages remains challenge. Our strategy is based on a regio-
selective deacetylation as shown in Sch. 1. The D-Glucose and L-Rhamnose
were chosen as the starting materials. 1,2,3,4,6-Penta-O-acetyl-b-D-gluco-
pyranose (1) and phenyl 4,6-O-benzylidene-1-thio-b-D-glucopyranoside (2)
were prepared as previously reported.[6] Acetylation of 2 with acetic
anhydride in pyridine (!3), followed by our regioselective deacetylation
method with hydrazine acetate in THF and CH2Cl2, afforded phenyl 2-O-
acetyl-4,6-O-benzylidene-1-thio-b-D-glucopyranoside (4) in good yield. Allyl
2-O-acetyl-3,4-di-O-benzoyl-a-L-rhamnopyranoside (6) was synthesized via
a four-step sequential reaction. 6 was then deallylated with PdCl2,[7] followed
by trichloroacetimidation with CCl3CN in the presence of DBU,[8] to give
2-O-acetyl-3,4-di-O-benzoyl-a-L-rhamnopyranosyl trichloacetimidate (7).
Similarly, the glycosyl donor 2,3,4,6-tetra-O-acetyl-a-D-glucopyranosyl tri-
chloacetimidate (5) was readily obtained by the selective 1-O-deacetylation
of 1 via the method of Excoffier[9] with hydrazine acetate and trichloro-
acetimidation.[10]
Figure 1. Structures of incanosides C, D and E.

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517
Scheme 1.
With the glucosyl acceptors 2 and 4 and rhamnosyl donor 7 in hand, the
key disaccharide 10 was directly synthesized by coupling of 7 with the
acceptor 4 in the presence of a catalytic amount of trimethylsilyl triflate
(TMSOTf) with high stereoselectivity in excellent yield. We also obtained 10
by the acetylation of 9 resulting from the regioselective coupling of 7 and 2
.
under BF3 OEt2 as the catalyst. In our case, we have not isolated the
intermediate orthoester 8.[11] This may be due to the long reaction time and
excess of catalyst (Sch. 2).
Disaccharide 11 is also a significant building block to synthesis of many
natural products, such as ballotetroside[12] and phenylpropanoid glycosides
from Lamiophlomis rotata[13] and Fernandoa adenophylla.[14] To get the free
20-OH of disaccharide, the chemoselective 20-O-deacetylation was usually
carried out in acid conditions,[15] which resulted in a undesired removing of
4,6-protecting group. Based on our regioselective and chemoselective
deacetylation method,[16] 10 was treated with 85% hydrazine hydrate in THF
to afford disaccharide 11 in good yield. Further glycosylation of 11 with donor
5 gave target trisaccharide 12 with an anomeric leaving group in excellent
yield.
In summary, we present the first synthesis of trisaccharide of natural
antioxidants and free radical scavengers incanosides C, D and E. The key step
of this concise and effective method involved the preparation of decisive

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Scheme 2.
disaccharide aceeptor from the phenyl 2-acetyl-3,4-di-O-benzoyl-a-L-
rhamnopyranosyl-(1 ! 3)-2-O-acetyl-4,6-O-benzylidene-1-thio-b-D-gluco-
pyranoside by regioselective and chemoselective deacetylation. The total
syntheses of incanosides C, D and E are in process.
EXPERIMENTAL
1H NMR spectra were determined in CDCl3 on a Bruker AVANCE
DMX-500 (500 MHz) with tetramethylsilane (Me4Si) as the internal standard.
Chemical shifts are expressed in ppm downfield from the internal Me4Si
absorption. Mass spectra were recorded with Bruker Daltonics APEXIII FT-
ICR mass spectrometer or Bruker Daltonics DataAnalysis 3.0 mass
spectrometer using the ESI technique to introduce the sample. Thin-layer
chromatography (TLC) was performed on silica gel GF254, detection being
affected by charring with 30% (v/v) sulfuric acid in methanol or sometimes by
UV detection. Column chromatography was conducted by elution of a column
(8/100 mm, 16/240 mm, 35/400 mm) of silica gel (100–200 mesh) and
EtOAc/petroleum ether (b.p. 60–908C) as the eluent. Melting points were
determined with a YANACO apparatus and were uncorrected. Elemental
analyses were performed at Carlo-Erba 1106 instrument.

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519
Phenyl 2-O-acetyl-4,6-O-benzylidene-1-thio-b-D-glucopyranoside
(4). To a solution of phenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-b-
D-glucopyranoside 3 (600 mg, 1.35 mmol) in dry THF and CH2Cl2 (1/1,
15 mL) was added hydrazine acetate (124 mg, 1.35 mmol). The mixture was
stirred at 308C for 4 h, then diluted with CH2Cl2 and washed with water and
brine. The organic phase was dried over MgSO4, filtered and concentrated
under reduced pressure. The crude oil was subject to column chromatography
on silica gel with petroleum ether/ethyl acetate (3 : 1) as the eluent to give 4
(350 mg, 64.4%) as a white solid. m.p. 192.4–194.58C 1H NMR d 7.48–7.32
(m, 10H, 2Ph-H), 5.53 (s, 1H, PhCH), 4.93 (dd, 1H, H-2), 4.73 (s, 1H, 10.0 Hz,
H-1), 4.36 (dd, 1H, H-6a), 3.88 (t, 1H, H-6b), 3.76 (t, 1H, H-4), 3.57–3.50
(m, 2H, H-3 and H-5), 2.17 (s, 3H, CH3CO) ppm.
Allyl 2-O-acetyl-3,4-di-O-Benzoyl-a-L-rhamnopyranoside (6). The
solution of trifluoromethanesulphonic acid (0.5 mL) and L-rhamnose mono-
hydrate (5 g, 27.4 mmol) in allyl alcohol (100 mL) was stirred at reflux for
3.5 h. After having cooled, the reaction mixture was neutralized with triethyla-
mine (1 mL), filtered and concentrated. After co-distillation with toluene
(3 ꢀ 30 mL), the residue was dissolved in a mixture of dry acetonitrile (25 mL)
and trimethyl orthoacetate (1.5 mL). p-Toluenesulfornic acid (50 mg) was
added, and the mixture was placed under partial vacuum on rotatory evaporator
and heated to 508C, and then stirred at 508C for 12 h. Triethylamine (1 mL) was
added and the mixture was concentrated to give a syrup. The syrup was
dissolved in 80% aqueous acetic acid (30 mL) and after 10 min the solution was
diluted with CH2Cl2 and washed with saturated aqueous NaHCO3 and water.
The organic phase was dried and concentrated in vacuum to give a syrup. The
syrup was then dissolved in pyridine (7 mL). The solution of benzoyl chloride
(7 mL) in CH2Cl2 (10 mL) was added at 08C. The mixture was stirred overnight
1
and then washed with N HCl, saturated aqueous NaHCO3 and water. The
purification of crude product through silica gel column with petroleum ether/
ethyl acetate (7 : 1, v/v) as the eluent gave 6 (8.22 g, 66%) as crystals. 1H NMR
d 7.97–7.32 (m, 10H, Bz-H), 5.93 (m, 1H, CH255CH–CH2), 5.71 (dd, 1H,
H-3), 5.53 (t, 1H, H-4), 5.47 (dd, 1H, H-2), 5.39–5.35 (m, 2H, CH255CH–
CH2), 4.90 (s, 1H, H-1), 4.28–4.24 (m, 1H, H-5), 4.16–4.06 (m, 2H,
CH255CH–CH2), 2.18 (s, 3H, CH3CO), 1.32 (d, 3H, H-6) ppm.
2-O-acetyl-3,4-di-O-benzoyl-a-L-rhamnopyranosyl trichloacetimi-
date (7). Allyl 2-O-acetyl-3,4-di-O-benzoyl-a-L-rhamnopyranoside (6)
(454 mg, 1 mmol) in 90% acetic acid (20 mL) containing sodium acetate
(586 mg, 3 mmol) was added PdCl2 (178 mg, 1 mmol) and the mixture was
stirred overnight. The mixture was diluted with CH2Cl2 and washed with
saturated aqueous NaHCO3 and water. The organic layer was concentrated
under reduced pressure and the obtained residue was passed eluent to give
crude 2-O-acetyl-3,4-di-O-benzoyl-a-L-rhamnopyranose, which was dis-

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Li and Wang
solved in dry CH2Cl2 (40 mL), then CCl3CN (0.2 mL, 2 mmol) and DBU
(28 mL, 0.18 mmol) were added. The reaction mixture was stirred at 08C for
3 h. Concentration of the reaction mixture followed by purification on flash
chromatography (2/1 petroleum ether/ethyl acetate as the eluent) gave 7
1
(507 mg, 91% for two steps) as crystals. H NMR d 8.79 (s, 1H,C55NH),
7.99–7.34 (m, 10H, Bz-H), 6.33 (s, 1H, H-1), 5.77–5.74 (m, 1H, H-3), 5.69–
5.63 (m, 2H, H-2 and H-4), 4.34-4.31 (m, 1H, H-5), 2.19 (s, 3H, CH3CO), 1.37
(d, 3H, H-6) ppm.
Phenyl 2-O-acetyl-3,4-di-O-benzoyl-a-L-rhamnopyranosyl-(1 ! 3)-
4,6-O-benzylidene-1-thio-b-D-glucopyranoside (9). 2-O-acetyl-3,4-di-O-
benzoyl-a-L-rhamnopyranosyl trichloroacetimidate 7 (335 mg, 0.6 mmol)
and phenyl 4,6-O-benzylidene-1-thio-b-D-glucopyranoside 2 (180 mg,
0.5 mmol) were together dried under high vacuum for 2–3 h, then dissolved
.
in dry CH2Cl2 (30 mL) and BF3 OEt2 (60 mL) was added dropwise at 2308C
under N2 atmosphere. The reaction mixture was stirred for 3 h. The reaction
mixture was neutralized with triethylamine, concentrated under reduced
pressure to dryness. Further purification by silic gel column chromatography
(1/1.5 petroleum ether/ethyl acetate as eluent) gave 9 (333 mg, 88%) as a
1
colorless solid. m.p. 171.6–173.48C; H NMR d 7.87–7.19 (m, 20H, Bz-H
and Ph-H), 5.63–5.61 (m, 2H, H-30 and PhCH), 5.53 (dd, 1H, H-20), 5.41 (t, 1H,
H-40), 5.35 (s, 1H, H-10), 4.61 (dd, 1H, 9.75 Hz, H-1), 4.46–4.41 (m, 2H, H-6a
and H-50), 3.98 (t, 1H, H-6b), 3.81 (t, 1H, H-4), 3.64 (t, 1H, H-3), 3.61–3.55
(m, 2H, H-2 and H-5), 2.12 (s, 3H, CH3CO), 0.92 (d, 3H, 6.10 Hz,H-60) ppm.
Phenyl 2-O-acetyl-3,4-di-O-benzoyl-a-L-rhamnopyranosyl-(1 ! 3)-
2-O-acetyl-4,6-O-benzylidene-1-thio-b-D-glucopyranoside (10). Method
A. Disaccharide 9 (302.5 mg, 0.4 mmol) was dissolved in a solution of fresh
pyridine/acetic anhydride (2/1, v/v, 8 mL), and the mixture was stirred
overnight at room temperature, then concentrated to dryness. Further
purification by column chromatography (2/1 petroleum either/ethyl acetate)
gave 10 (313 mg, 98%).
Method B. The mixture of 7 (335 g, 0.6 mmol) and phenyl 2-O-acetyl-
4,6-O-benzylidene-1-thio-b-D-glucopyranoside 4 (201 mg, 0.5 mmol) was
dried under high vacuum for 2–3 h, then dissolved in dry CH2Cl2 (30 mL).
TMSOTf (10 mL, 0.1 equiv) in CH2Cl2 (mL) was added dropwise at 2458C
under N2. The reaction mixture was stirred for 4 h and then neutralized with
triethylamine, concentrated under reduced pressure to dryness. Further
purification by column chromatography (1/1.5 petroleum ether/ethyl acetate
as eluent) gave 10 (367 mg, 92%) as a colorless solid. m.p. 186.7–189.38C;
1H NMR d 7.88–7.16 (m, 20H, Bz-H and Ph-H), 5.69 (dd, 1H, H-30), 5.61
(s, 1H, PhCH), 5.38 (t, 1H, H-40), 5.18–5.14 (m, 2H, H-2 and H-40), 5.04
(s, 1H, H-10), 4.74 (dd, 1H, 10.08 Hz, H-1), 4.44–4.40 (dd, 1H, H-6a), 4.35–
4.31 (m, 1H, H-50), 4.01 (t, 1H, H-6b), 3.82 (t, 1H, H-4), 3.75 (t, 1H, H-3), 3.57

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521
(m, 1H, H-5), 2.17 (s, 3H, CH3CO), 2.13 (s, 3H, CH3CO), 0.72 (d, 3H,
6.09 Hz, H-60) ppm.
Phenyl 3,4-di-O-benzoyl-a-L-rhamnopyranosyl-(1 ! 3)-2-O-acetyl-
4,6-O-benzylidene-1-thio-b-D-glucopyranoside (11). To a solution of 10
(1.6 g, 2.0 mmol) in 25 mL THF was added 3.0 equiv of 85% hydrazine
hydrate (0.38 mL). The mixture was stirred at room temperature for 11 h, then
quenched by the addition of H2O (20 mL) and extracted with CH2Cl2. The
combined organic layers were washed with brine, dried over MgSO4, filtered
and concentrated under reduced pressure. The crude product was subject to
column chromatography on silica gel with petroleum ether/ethyl acetate
(3 : 1) as the eluent to give 11 (1.12 g, 73.8%). m.p. 170.2–172.58C; 1H NMR
d 7.95–7.17 (m, 20H, Bz-H and Ph-H), 5.61 (s, 1H, PhCH), 5.53 (dd, 1H,
H-30), 5.41 (t, 1H, H-40), 5.09 (t, 1H, H-2), 5.00 (s, 1H, H-10), 4.74 (dd, 1H,
10.09 Hz, H-1), 4.44–4.40 (dd, 1H, H-6a), 4.37–4.34 (m, 1H, H-50), 4.15
(br, 1H, H-20), 4.08 (t, 1H, H-6b), 3.82 (t, 1H, H-4), 3.71 (t, 1H, H-3), 3.60–
3.56 (m, 1H, H-5), 2.14 (s, 3H, CH3CO), 0.80 (d, 3H, 6.15 Hz, H-60). Anal.
Calcd for C41H40O12S: C, 65.07; H, 5.23; S, 4.24. Found: C, 64.38; H, 5.33;
S, 4.17. MS(ESI): 779 ([M þ Na]þ).
Phenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl-(1 ! 2)- 3,4-di-O-
benzoyl-a-L-rhamnopyranosyl-(1 ! 3)-2-O-acetyl-4,6-O-benzylidene-1-
thio-b-D-glucopyrano side (12). The disaccharide acceptor 11 (151 mg,
0.2 mmol) and glucosyl donor 5 (128 mg, 0.26 mmol) were dried under high
vacuum for 2–3 h, then dissolved in dry CH2Cl2 (15 mL) and 24 mL of a 0.2N
.
solution of BF3 OEt2 was added dropwise at 2308C under N2. The reaction
mixture was stirred for 3 h, and then neutralized with triethylamine, concen-
trated under reduced pressure to dryness. Further purification by column
chromatography (1/1.5 petroleum ether/ethyl acetate as eluent) gave 12
1
(197 mg, 91%) as a colorless solid. m.p. 264.3–275.88C; H NMR d 7.95–
7.19 (m, 20H, Bz-H and Ph-H), 5.61 (s, 1H, PhCH), 5.53 (dd, 1H, H-30), 5.45
(t, 1H, H-300), 5.40 (br, 2H, H-10 and H-40), 5.12–5.10 (m, 2H, H-2 and H-200),
4.62 (dd, 1H, 9.74 Hz, H-1), 4.44–4.40 (m, 2H, H-6a and H-400), 4.33 (br, 1H,
H-20), 4.23–4.20 (m, 2H, H-50 and H-6a00), 4.08 (dd, 1H, 6.74 Hz, H-100), 4.01
(t, 1H, H-6b), 3.87–3.80 (m, 2H, H-6b00 and H-4), 3.63 (t, 1H, H-3), 3.60–3.56
(m, 2H, H-500 and H-5), 2.11–2.00 (5s, 15H, 5CH3CO), 0.98 (d, 3H, 6.70 Hz,
H-60). HRMS(ESI): Calcd for C56H60O20S: 1083.3320([M-H]þ). Found:
1083.3344([M-H]þ).
ACKNOWLEDGMENTS
The work was supported by The National Natural Science Foundation of
China (No. 20272051) and by The Teaching and Research Award Program

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for Outstanding Young Teachers in Higher Education Institutions of MOE,
P.R.C.
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Received in Japan June 9, 2003

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