1-O-tert-Butyl-2-O-benzyl-4-O-isobutyl-3,6-dideoxy-6-azido-β-L-glucopyranoside

Base Information

Chemical Name:1-O-tert-Butyl-2-O-benzyl-4-O-isobutyl-3,6-dideoxy-6-azido-β-L-glucopyranoside
CAS No.:259726-47-1
Molecular Formula:C₂₁H₃₃N₃O₄
Molecular Weight:391.511
Hs Code.:

Synonyms:1-O-tert-Butyl-2-O-benzyl-4-O-isobutyl-3,6-dideoxy-6-azido-β-L-glucopyranoside

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Chemical Property of 1-O-tert-Butyl-2-O-benzyl-4-O-isobutyl-3,6-dideoxy-6-azido-β-L-glucopyranoside

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Technology Process of 1-O-tert-Butyl-2-O-benzyl-4-O-isobutyl-3,6-dideoxy-6-azido-β-L-glucopyranoside

There total 9 articles about 1-O-tert-Butyl-2-O-benzyl-4-O-isobutyl-3,6-dideoxy-6-azido-β-L-glucopyranoside 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: 86.2%

: 78-77-3
Isobutyl bromide

: 311-28-4
tetra-(n-butyl)ammonium iodide

: 259726-46-0
1-O-tert-Butyl-2-O-benzyl-3,6-dideoxy-6-azido-β-L-glucopyranoside

: 259726-47-1
1-O-tert-Butyl-2-O-benzyl-4-O-isobutyl-3,6-dideoxy-6-azido-β-L-glucopyranoside

Guidance literature:: With NaH; In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate;

Reference yield: 86.0%

: 78-77-3
Isobutyl bromide

: 259726-46-0
1-O-tert-Butyl-2-O-benzyl-3,6-dideoxy-6-azido-β-L-glucopyranoside

: 259726-47-1
1-O-tert-Butyl-2-O-benzyl-4-O-isobutyl-3,6-dideoxy-6-azido-β-L-glucopyranoside

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;
DOI:10.1016/S0960-894X(98)00575-7

Reference yield:

: 259726-43-7
(2R,3S,5R,6S)-2-tert-Butoxy-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

: 259726-47-1
1-O-tert-Butyl-2-O-benzyl-4-O-isobutyl-3,6-dideoxy-6-azido-β-L-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: PPTS

2: 93 percent / NaH, TBAI / tetrahydrofuran

3: DIBAL / CH₂Cl₂

4: Et₃N, DMAP / CH₂Cl₂

5: NaN₃ / dimethylformamide / 90 °C

6: 74 percent / DDQ / CH₂Cl₂; H₂O

7: 86 percent / NaH, TBAI / tetrahydrofuran

With dmap; sodium azide; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(98)00575-7