methyl O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranoside)

Base Information

Chemical Name:methyl O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranoside)
CAS No.:273749-67-0
Molecular Formula:C₅₈H₇₀N₂O₂₀
Molecular Weight:1115.2
Hs Code.:

methyl O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranoside)

Synonyms:methyl O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranoside)

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Chemical Property of methyl O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranoside)

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Technology Process of methyl O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranoside)

There total 16 articles about methyl O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranoside) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: (2R,3S,4R)-5-Azido-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol

: 273749-67-0
methyl O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranoside)

Guidance literature:: Multi-step reaction with 9 steps

1.1: 424 mg / p-TsOH*H₂O / acetonitrile / 6 h / 20 °C

2.1: 83 percent / Tf₂O; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -60 - -30 °C

3.1: 442 mg / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 24 h / 60 °C

4.1: NaH / dimethylformamide; various solvent(s)

4.2: 82 percent / dimethylformamide; various solvent(s) / 6 h / 0 °C

5.1: 91 percent / NaBH₃CN; TFA; 3 Angstroem molecular sieves / dimethylformamide / 8 h / 0 °C

6.1: 86 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 0 - 20 °C

7.1: Cd / dimethylformamide; acetic acid / 8 h / 20 °C

8.1: thioacetic acid / pyridine / 12 h / 20 °C

9.1: 288 mg / pyridine / 0.5 h

With pyridine; lithium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; tiolacetic acid; cadmium; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1.1: Deacetylation / 2.1: Condensation / 3.1: Hydrolysis / 4.1: Metallation / 4.2: Benzylation / 5.1: Reduction / 6.1: Condensation / 7.1: Reduction / 8.1: Reduction / 9.1: Acetylation;
DOI:10.1021/ol0057075

Reference yield:

: phenyl 2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranosyl sulfoxide

: 273749-67-0
methyl O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranoside)

Guidance literature:: Multi-step reaction with 8 steps

1.1: 83 percent / Tf₂O; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -60 - -30 °C

2.1: 442 mg / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 24 h / 60 °C

3.1: NaH / dimethylformamide; various solvent(s)

3.2: 82 percent / dimethylformamide; various solvent(s) / 6 h / 0 °C

4.1: 91 percent / NaBH₃CN; TFA; 3 Angstroem molecular sieves / dimethylformamide / 8 h / 0 °C

5.1: 86 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 0 - 20 °C

6.1: Cd / dimethylformamide; acetic acid / 8 h / 20 °C

7.1: thioacetic acid / pyridine / 12 h / 20 °C

8.1: 288 mg / pyridine / 0.5 h

With pyridine; lithium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; sodium hydride; sodium cyanoborohydride; trifluoroacetic acid; tiolacetic acid; cadmium; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 1.1: Condensation / 2.1: Hydrolysis / 3.1: Metallation / 3.2: Benzylation / 4.1: Reduction / 5.1: Condensation / 6.1: Reduction / 7.1: Reduction / 8.1: Acetylation;
DOI:10.1021/ol0057075

Reference yield:

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1
(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 273749-67-0
methyl O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzyl-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranoside)

Guidance literature:: Multi-step reaction with 11 steps

1.1: 88 percent / p-TsOH*H₂O / dimethylformamide / 2 h / 50 °C

2.1: 92 percent / DMAP / pyridine / 12 h / Heating

3.1: 69 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.33 h / -78 °C

4.1: 83 percent / Tf₂O; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -60 - -30 °C

5.1: 442 mg / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 24 h / 60 °C

6.1: NaH / dimethylformamide; various solvent(s)

6.2: 82 percent / dimethylformamide; various solvent(s) / 6 h / 0 °C

7.1: 91 percent / NaBH₃CN; TFA; 3 Angstroem molecular sieves / dimethylformamide / 8 h / 0 °C

8.1: 86 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 0 - 20 °C

9.1: Cd / dimethylformamide; acetic acid / 8 h / 20 °C

10.1: thioacetic acid / pyridine / 12 h / 20 °C

11.1: 288 mg / pyridine / 0.5 h

With pyridine; dmap; lithium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; tiolacetic acid; cadmium; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Acylation / 3.1: Oxidation / 4.1: Condensation / 5.1: Hydrolysis / 6.1: Metallation / 6.2: Benzylation / 7.1: Reduction / 8.1: Condensation / 9.1: Reduction / 10.1: Reduction / 11.1: Acetylation;
DOI:10.1021/ol0057075