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

Base Information

Chemical Name:5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-tert-butoxycarbonyl-3,2',3'-triazidoneamine
CAS No.:860795-52-4
Molecular Formula:C₃₇H₄₉N₁₃O₁₁
Molecular Weight:851.877
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-tert-butoxycarbonyl-3,2',3'-triazidoneamine

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Technology Process of 5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-tert-butoxycarbonyl-3,2',3'-triazidoneamine

There total 8 articles about 5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-tert-butoxycarbonyl-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%

: 860795-44-4
6-O-benzoyl-3',4'-di-O-benzyl-1-N-tert-butoxycarbonyl-3,2',3'-triazidoneamine

: 485809-80-1
4-azido-2,3-di-O-acetyl-4,6-dideoxy-α-D-glucopyranosyl trichloroacetimidate

: 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

Guidance literature:: 6-O-benzoyl-3',4'-di-O-benzyl-1-N-tert-butoxycarbonyl-3,2',3'-triazidoneamine; 4-azido-2,3-di-O-acetyl-4,6-dideoxy-α-D-glucopyranosyl trichloroacetimidate; With boron trifluoride diethyl etherate; In dichloromethane;

With sodium methylate; In tetrahydrofuran; methanol;

Reference yield:

: Benzoic acid (1S,2S,3R,4S,6R)-4-azido-3-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-tert-butoxycarbonylamino-2-((2S,3R,4S,5R,6R)-3,4-diacetoxy-5-azido-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyl ester

: 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

Guidance literature:: With sodium methylate; In tetrahydrofuran; methanol;
DOI:10.1021/ol051045d

Reference yield:

: C₃₂H₃₈N₁₂O₆

: 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

Guidance literature:: Multi-step reaction with 6 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

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