4-O-(3-azido-3-deoxy-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine

Base Information

Chemical Name:4-O-(3-azido-3-deoxy-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine
CAS No.:236115-75-6
Molecular Formula:C₃₃H₃₇N₉O₇
Molecular Weight:671.713
Hs Code.:

Synonyms:4-O-(3-azido-3-deoxy-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine

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Chemical Property of 4-O-(3-azido-3-deoxy-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine

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Technology Process of 4-O-(3-azido-3-deoxy-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine

There total 9 articles about 4-O-(3-azido-3-deoxy-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine 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: 100.0%

: Acetic acid (1S,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-((2S,3R,4S,5S,6R)-4-azido-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl ester

: 236115-75-6
4-O-(3-azido-3-deoxy-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine

Guidance literature:: With sodium methylate; In tetrahydrofuran; methanol; for 21h; Ambient temperature;
DOI:10.1021/ja9910356

Reference yield:

: 2037-48-1,731753-11-0
2-deoxystreptamine

: 236115-75-6
4-O-(3-azido-3-deoxy-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine

Guidance literature:: Multi-step reaction with 5 steps

1: TfN₃, Et₃N, CuSO₄ / CH₂Cl₂; methanol / 21 h / Ambient temperature

2: pyridine, DMAP / 23 h / Ambient temperature

3: 71 percent / Novozym 435 (Candida antarctica lipase), sodium phosphate buffer (pH 6.2) / toluene / 72 h / Ambient temperature

4: TfOH, NIS / diethyl ether; CH₂Cl₂ / 0.5 h / -15 °C

5: 100 percent / NaOMe / tetrahydrofuran; methanol / 21 h / Ambient temperature

With pyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium phosphate buffer; Novozym 435 (Candida antarctica lipase); triflic azide; sodium methylate; copper(II) sulfate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja9910356

Reference yield:

: 185114-94-7,155417-78-0
1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

: 236115-75-6
4-O-(3-azido-3-deoxy-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine

Guidance literature:: Multi-step reaction with 5 steps

1: 64 percent / BF₃*Et₂O / CHCl₃ / 22 h / Ambient temperature

2: 100 percent / NaOMe / methanol / 17.5 h / Ambient temperature

3: 85 percent / NaH / dimethylformamide / 4 h / 0 - 20 °C

4: TfOH, NIS / diethyl ether; CH₂Cl₂ / 0.5 h / -15 °C

5: 100 percent / NaOMe / tetrahydrofuran; methanol / 21 h / Ambient temperature

With N-iodo-succinimide; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/ja9910356