3,4,6-tri-O-benzyl-2-azido-2-deoxy-D-glucopyranosyl-α(1->1)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol

Base Information

Chemical Name:3,4,6-tri-O-benzyl-2-azido-2-deoxy-D-glucopyranosyl-α(1->1)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol
CAS No.:270595-84-1
Molecular Formula:C₆₁H₆₃N₃O₁₀
Molecular Weight:998.185
Hs Code.:

Synonyms:3,4,6-tri-O-benzyl-2-azido-2-deoxy-D-glucopyranosyl-α(1->1)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol

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Chemical Property of 3,4,6-tri-O-benzyl-2-azido-2-deoxy-D-glucopyranosyl-α(1->1)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol

Chemical Property:

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Technology Process of 3,4,6-tri-O-benzyl-2-azido-2-deoxy-D-glucopyranosyl-α(1->1)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol

There total 14 articles about 3,4,6-tri-O-benzyl-2-azido-2-deoxy-D-glucopyranosyl-α(1->1)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol 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: 74.0%

: 270595-83-0
6-O-allyl-1-O-(3,4,6-tri-O-benzyl-2-azido-2-deoxy-α-D-glucopyranosyl)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol

: 270595-84-1
3,4,6-tri-O-benzyl-2-azido-2-deoxy-D-glucopyranosyl-α(1->1)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol

Guidance literature:: With sodium acetate; palladium dichloride; In water; acetic acid; for 6.5h;
DOI:10.1002/(SICI)1099-0690(200004)2000:8<1539::AID-EJOC1539>3.0.CO;2-2

Reference yield: 60.0%

: 99049-62-4
2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

: 110550-24-8
1D-2,3,4,5-tetra-O-benzyl-chiro-inositol

: 3,4,6-tri-O-benzyl-2-azido-2-deoxy-D-glucopyranosyl-β(1->1)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol

: di(3,4,6-tri-O-benzyl-2-azido-2-deoxy-D-glucopyranosyl)-α,α(1->1:1->6)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol

: 270595-84-1
3,4,6-tri-O-benzyl-2-azido-2-deoxy-D-glucopyranosyl-α(1->1)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -25 ℃; for 1h;
DOI:10.1055/s-2005-871945

Reference yield:

: D-chiro-inositol

: 270595-84-1
3,4,6-tri-O-benzyl-2-azido-2-deoxy-D-glucopyranosyl-α(1->1)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 76 percent / imidazole / DMAP / dimethylformamide / 3.5 h

2.1: 80 percent / PPh₃; DEAD / tetrahydrofuran / 7 h / 25 °C

3.1: 77 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h / 25 °C

4.1: 90 percent / NaI; (i-Pr)2EtN / dioxane / 80 °C

5.1: TBAF / tetrahydrofuran / 2 h / 25 °C

6.1: pyridine / tetrahydrofuran / 18 h / 25 °C

7.1: NaOMe / methanol / 0.5 h / 25 °C

7.2: 89 percent / NaH / dimethylformamide

8.1: 86 percent / PhSH; BF₃Et₂O / CH₂Cl₂ / 0.5 h / -10 °C

9.1: 44 percent / MS 4 Angstroem; TMSOTf / CH₂Cl₂ / 1 h / 25 °C

10.1: NaOMe / methanol / 0.17 h / 25 °C

11.1: 99 percent / NaH / dimethylformamide / 1 h

12.1: 74 percent / NaOAc; PdCl₂ / acetic acid; H₂O / 6.5 h

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; sodium acetate; sodium hydride; thiophenol; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; palladium dichloride; diethylazodicarboxylate; dmap; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Epoxidation / 3.1: Etherification / 4.1: Etherification / 5.1: desilylation / 6.1: Acetylation / 7.1: Deacetylation / 7.2: Alkylation / 8.1: deprotection / 9.1: Etherification / 10.1: Deacetylation / 11.1: benzylation / 12.1: deallylation;
DOI:10.1002/(SICI)1099-0690(200004)2000:8<1539::AID-EJOC1539>3.0.CO;2-2