6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(6-azido-3-oxa-2,3,4,6-tetradeoxy-α-D-glycero-hexopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine

Base Information

Chemical Name:6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(6-azido-3-oxa-2,3,4,6-tetradeoxy-α-D-glycero-hexopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine
CAS No.:179533-33-6
Molecular Formula:C₄₇H₅₆N₆O₁₆S₃
Molecular Weight:1057.19
Hs Code.:

6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(6-azido-3-oxa-2,3,4,6-tetradeoxy-α-D-glycero-hexopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine

Synonyms:6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(6-azido-3-oxa-2,3,4,6-tetradeoxy-α-D-glycero-hexopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine

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Chemical Property of 6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(6-azido-3-oxa-2,3,4,6-tetradeoxy-α-D-glycero-hexopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine

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Technology Process of 6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(6-azido-3-oxa-2,3,4,6-tetradeoxy-α-D-glycero-hexopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine

There total 13 articles about 6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(6-azido-3-oxa-2,3,4,6-tetradeoxy-α-D-glycero-hexopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine 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: 30.0%

: ethyl 6-azido-3-oxa-2,3,4,6-tetradeoxy-1-thio-D-glycero-hexopyranoside

: 179533-32-5
6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine

: 179533-33-6
6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(6-azido-3-oxa-2,3,4,6-tetradeoxy-α-D-glycero-hexopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 2.5h;
DOI:10.1016/0008-6215(96)00051-1

Reference yield:

: 179533-23-4
(2S)-3-O-(2,2-dimethoxyethyl)-1,2-O-isopropylideneglycerol

: 179533-33-6
6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(6-azido-3-oxa-2,3,4,6-tetradeoxy-α-D-glycero-hexopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine

Guidance literature:: Multi-step reaction with 7 steps

1: 33 percent / HCl / methanol / 1 h / 45 °C

2: 83 percent / pyridine / CH₂Cl₂ / 14 h / 20 °C

3: 100 percent / NaN₃ / dimethylformamide / 3.5 h / 80 °C

4: 87 percent / HCl / acetic acid; H₂O / 20 h / 60 °C

5: 60 percent / pyridine / 5 h / 20 °C

6: 73 percent / CF₃SO₃SiMe₃ / 1,2-dichloro-ethane / 0.25 h / 20 °C

7: 30 percent / N-iodosuccinimide; molecular sieves 4A; CF₃SO₃H / CH₂Cl₂ / 2.5 h / 20 °C

With pyridine; hydrogenchloride; N-iodo-succinimide; sodium azide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In methanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: Cyclization / 2: Tosylation / 3: Substitution / 4: Hydrolysis / 5: Acetylation / 6: thioglycosylation / 7: glycosylation;
DOI:10.1016/0008-6215(96)00051-1

Reference yield:

: 179533-25-6
methyl 3-oxa-2,3,4-trideoxy-α-D-glycero-hexopyranoside

: 179533-33-6
6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(6-azido-3-oxa-2,3,4,6-tetradeoxy-α-D-glycero-hexopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / pyridine / CH₂Cl₂ / 14 h / 20 °C

2: 100 percent / NaN₃ / dimethylformamide / 3.5 h / 80 °C

3: 87 percent / HCl / acetic acid; H₂O / 20 h / 60 °C

4: 60 percent / pyridine / 5 h / 20 °C

5: 73 percent / CF₃SO₃SiMe₃ / 1,2-dichloro-ethane / 0.25 h / 20 °C

6: 30 percent / N-iodosuccinimide; molecular sieves 4A; CF₃SO₃H / CH₂Cl₂ / 2.5 h / 20 °C

With pyridine; hydrogenchloride; N-iodo-succinimide; sodium azide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; water; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1: Tosylation / 2: Substitution / 3: Hydrolysis / 4: Acetylation / 5: thioglycosylation / 6: glycosylation;
DOI:10.1016/0008-6215(96)00051-1