2-O-acetyl-3,4,6-trideoxy-4-azido-β-glucopyranoside-(1→4)-benzyl 2-deoxy-2-azido-3-O-triisopropylsilyl-β-xylopyranoside

Base Information

Chemical Name:2-O-acetyl-3,4,6-trideoxy-4-azido-β-glucopyranoside-(1→4)-benzyl 2-deoxy-2-azido-3-O-triisopropylsilyl-β-xylopyranoside
CAS No.:1416351-55-7
Molecular Formula:C₂₉H₄₆N₆O₇Si
Molecular Weight:618.806
Hs Code.:

Synonyms:2-O-acetyl-3,4,6-trideoxy-4-azido-β-glucopyranoside-(1→4)-benzyl 2-deoxy-2-azido-3-O-triisopropylsilyl-β-xylopyranoside

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Chemical Property of 2-O-acetyl-3,4,6-trideoxy-4-azido-β-glucopyranoside-(1→4)-benzyl 2-deoxy-2-azido-3-O-triisopropylsilyl-β-xylopyranoside

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Technology Process of 2-O-acetyl-3,4,6-trideoxy-4-azido-β-glucopyranoside-(1→4)-benzyl 2-deoxy-2-azido-3-O-triisopropylsilyl-β-xylopyranoside

There total 12 articles about 2-O-acetyl-3,4,6-trideoxy-4-azido-β-glucopyranoside-(1→4)-benzyl 2-deoxy-2-azido-3-O-triisopropylsilyl-β-xylopyranoside 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: 82.0%

: phenyl 2-O-acetyl-3,4,6-trideoxy-4-azido-1-thioglucopyranoside

: 1416351-52-4
benzyl 2-deoxy-2-azido-3-O-triisopropylsilyl-β-xylopyranoside

: 1416351-55-7
2-O-acetyl-3,4,6-trideoxy-4-azido-β-glucopyranoside-(1→4)-benzyl 2-deoxy-2-azido-3-O-triisopropylsilyl-β-xylopyranoside

Guidance literature:: With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃; Inert atmosphere; Molecular sieve;
DOI:10.1021/ol303093z

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
D-lyxose

: 1416351-55-7
2-O-acetyl-3,4,6-trideoxy-4-azido-β-glucopyranoside-(1→4)-benzyl 2-deoxy-2-azido-3-O-triisopropylsilyl-β-xylopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1.1: triethylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2.1: trimethylsilyl iodide / dichloromethane / Inert atmosphere

2.2: Inert atmosphere

3.1: pyridine / 0 - 20 °C / Inert atmosphere

4.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

4.2: 19 h / 20 °C / Inert atmosphere; Darkness

5.1: sodium methylate / methanol / 0 - 20 °C / Inert atmosphere

6.1: 2,6-dimethylpyridine / tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere

7.1: pyridine / cyclohexane / 2 h / -10 °C / Inert atmosphere

8.1: sodium azide / dimethyl sulfoxide / 14 h / 20 °C

9.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 20 °C / Inert atmosphere

10.1: mercury(II) oxide; mercury dichloride; water / acetone / 2 h / 20 °C / Inert atmosphere

11.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Inert atmosphere; Molecular sieve

With pyridine; 2,6-dimethylpyridine; N-iodo-succinimide; sodium azide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylsilyl iodide; trimethylsilyl trifluoromethanesulfonate; water; hydrogen; sodium methylate; triethylamine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol303093z

Reference yield:

: 14251-20-8,18622-98-5,18623-23-9,18623-24-0,18623-27-3,18771-81-8,20585-61-9,32166-72-6,32166-73-7,55555-45-8,56271-64-8,56271-65-9,56271-66-0,56271-67-1,56271-70-6,94942-10-6
1,2,3,4-tetra-O-trimethylsilyl-D-lyxopyranose

: 1416351-55-7
2-O-acetyl-3,4,6-trideoxy-4-azido-β-glucopyranoside-(1→4)-benzyl 2-deoxy-2-azido-3-O-triisopropylsilyl-β-xylopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1.1: trimethylsilyl iodide / dichloromethane / Inert atmosphere

1.2: Inert atmosphere

2.1: pyridine / 0 - 20 °C / Inert atmosphere

3.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

3.2: 19 h / 20 °C / Inert atmosphere; Darkness

4.1: sodium methylate / methanol / 0 - 20 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere

6.1: pyridine / cyclohexane / 2 h / -10 °C / Inert atmosphere

7.1: sodium azide / dimethyl sulfoxide / 14 h / 20 °C

8.1: (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; hydrogen / tetrahydrofuran / 20 °C / Inert atmosphere

9.1: mercury(II) oxide; mercury dichloride; water / acetone / 2 h / 20 °C / Inert atmosphere

10.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Inert atmosphere; Molecular sieve

With pyridine; 2,6-dimethylpyridine; N-iodo-succinimide; sodium azide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylsilyl iodide; trimethylsilyl trifluoromethanesulfonate; water; hydrogen; sodium methylate; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; dimethyl sulfoxide; acetone;
DOI:10.1021/ol303093z