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114869-97-5

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Basic Information
CAS No.: 114869-97-5
Name: a-D-Glucopyranoside, methyl4-O-[2-O-acetyl-6-methyl-3-O-(phenylmethyl)-a-L-idopyranuronosyl]-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-,6-acetate
Article Data: 2
Molecular Structure:
Molecular Structure of 114869-97-5 (a-D-Glucopyranoside, methyl4-O-[2-O-acetyl-6-methyl-3-O-(phenylmethyl)-a-L-idopyranuronosyl]-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-,6-acetate)
Formula: C40H47 N O15
Molecular Weight: 781.811
Synonyms: a-D-Glucopyranoside,methyl 4-O-[2-O-acetyl-6-methyl-3-O-(phenylmethyl)-a-L-idopyranuronosyl]-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-,6-acetate
PSA: 196.33000
LogP: 3.16670
Related products
Synthetic route
114869-96-4

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

114869-97-5

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Conditions
ConditionsYield
With 2,6-dimethylpyridine; dithiocarbonic acid hydrazide; acetic acid In methanol; dichloromethane for 0.166667h;85%
256486-94-9

methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside

18107-18-1

diazomethyl-trimethyl-silane

114869-97-5

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Conditions
ConditionsYield
Esterification;
3006-58-4, 13030-01-8, 42890-10-8, 42973-23-9, 77059-32-6, 121785-09-9, 7474-40-0

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

114869-97-5

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: HCl
2: CSA / tetrahydrofuran
3: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
4: aq. AcOH
5: pyridine / CH2Cl2
6: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
7: NaOMe; MeOH
8: CSA / acetone
9: DMAP; pyridine / CH2Cl2
10: aq. AcOH
11: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
12: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
1078691-95-8

(+)-D-glucosamine hydrochloride

114869-97-5

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: aq. Na2CO3
2: HCl
3: CSA / tetrahydrofuran
4: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
5: aq. AcOH
6: pyridine / CH2Cl2
7: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
8: NaOMe; MeOH
9: CSA / acetone
10: DMAP; pyridine / CH2Cl2
11: aq. AcOH
12: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
13: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
87907-35-5

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside

114869-97-5

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: pyridine / CH2Cl2
2: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
3: NaOMe; MeOH
4: CSA / acetone
5: DMAP; pyridine / CH2Cl2
6: aq. AcOH
7: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
8: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
Multi-step reaction with 3 steps
1: 59 percent / CH2Cl2 / Heating
2: 1) 2,6-dimethylpyridinium perchlorate / 1) chlorobenzene, 20 min, reflux, 2) reflux, 15 min
3: 85 percent / 2,6-dimethylpyridine, hydrazinedithiocarbonate, acetic acid / methanol; CH2Cl2 / 0.17 h
View Scheme
501-53-1

benzyl chloroformate

PhMgX

PhMgX

114869-97-5

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: aq. Na2CO3
2: HCl
3: CSA / tetrahydrofuran
4: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
5: aq. AcOH
6: pyridine / CH2Cl2
7: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
8: NaOMe; MeOH
9: CSA / acetone
10: DMAP; pyridine / CH2Cl2
11: aq. AcOH
12: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
13: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
114869-95-3

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

114869-97-5

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
2: NaOMe; MeOH
3: CSA / acetone
4: DMAP; pyridine / CH2Cl2
5: aq. AcOH
6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
7: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
Multi-step reaction with 2 steps
1: 1) 2,6-dimethylpyridinium perchlorate / 1) chlorobenzene, 20 min, reflux, 2) reflux, 15 min
2: 85 percent / 2,6-dimethylpyridine, hydrazinedithiocarbonate, acetic acid / methanol; CH2Cl2 / 0.17 h
View Scheme
87907-34-4

methyl 3-O-benzyl-4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside

114869-97-5

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: aq. AcOH
2: pyridine / CH2Cl2
3: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
4: NaOMe; MeOH
5: CSA / acetone
6: DMAP; pyridine / CH2Cl2
7: aq. AcOH
8: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
9: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
60076-41-7

methyl 4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside

114869-97-5

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 78 percent / BaO; Ba(OH)2*8H2O / dimethylformamide
2: aq. AcOH
3: pyridine / CH2Cl2
4: 75 percent / Sn(OTf)2 / CH2Cl2 / 0 °C
5: NaOMe; MeOH
6: CSA / acetone
7: DMAP; pyridine / CH2Cl2
8: aq. AcOH
9: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
10: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme

[(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((2S,3R,4S,5R,6S)-4-benzyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

114869-97-5

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: CSA / acetone
2: DMAP; pyridine / CH2Cl2
3: aq. AcOH
4: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr
5: NaClO2; aq. NaH2PO4 / 2-methyl-propan-2-ol
View Scheme
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