5-O-(4-azido-3,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-3,2',3'-triazidoneamine

Base Information

Chemical Name:5-O-(4-azido-3,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-3,2',3'-triazidoneamine
CAS No.:860795-53-5
Molecular Formula:C₄₄H₅₄N₁₄O₁₃
Molecular Weight:986.999
Hs Code.:

Synonyms:5-O-(4-azido-3,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-3,2',3'-triazidoneamine

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Chemical Property of 5-O-(4-azido-3,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-3,2',3'-triazidoneamine

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Technology Process of 5-O-(4-azido-3,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-3,2',3'-triazidoneamine

There total 11 articles about 5-O-(4-azido-3,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-3,2',3'-triazidoneamine 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: 62.0%

: 860795-52-4
5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-tert-butoxycarbonyl-3,2',3'-triazidoneamine

: 40371-50-4
S-4-benzyloxycarbonylamino-2-hydroxybutyric acid

: 860795-53-5
5-O-(4-azido-3,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-3,2',3'-triazidoneamine

Guidance literature:: 5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-tert-butoxycarbonyl-3,2',3'-triazidoneamine; With trifluoroacetic acid; In dichloromethane;

S-4-benzyloxycarbonylamino-2-hydroxybutyric acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;

Reference yield:

: 860795-43-3
3',4'-di-O-benzyl-1-N-tert-butoxycarbonyl-3,2',3'-triazidoneamine

: 860795-53-5
5-O-(4-azido-3,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-3,2',3'-triazidoneamine

Guidance literature:: Multi-step reaction with 5 steps

1: 87 percent / DIPEA / CH₂Cl₂ / -50 - 0 °C

2: BF₃*OEt₂ / CH₂Cl₂

3: NaOMe / tetrahydrofuran; methanol

4: TFA / CH₂Cl₂ / 3 h / 20 °C

5: DCC; N-hydroxysuccinimide; Et₃N / tetrahydrofuran

With 1-hydroxy-pyrrolidine-2,5-dione; boron trifluoride diethyl etherate; sodium methylate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol051045d

Reference yield:

: C₃₂H₃₈N₁₂O₆

: 860795-53-5
5-O-(4-azido-3,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-3,2',3'-triazidoneamine

Guidance literature:: Multi-step reaction with 8 steps

1.1: 4.52 g / glacial AcOH / dioxane; H₂O / 60 - 65 °C

2.1: 77 percent / Et₃N; DMAP / CH₂Cl₂ / Heating

3.1: Me₃P / toluene / -78 - 10 °C

3.2: 33 percent / NaOMe / methanol; tetrahydrofuran / 2 h / 20 °C

4.1: 87 percent / DIPEA / CH₂Cl₂ / -50 - 0 °C

5.1: BF₃*OEt₂ / CH₂Cl₂

6.1: NaOMe / tetrahydrofuran; methanol

7.1: TFA / CH₂Cl₂ / 3 h / 20 °C

8.1: DCC; N-hydroxysuccinimide; Et₃N / tetrahydrofuran

With dmap; 1-hydroxy-pyrrolidine-2,5-dione; boron trifluoride diethyl etherate; sodium methylate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; toluene; 3.1: Staudinger reaction;
DOI:10.1021/ol051045d