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

Base Information

• Chemical Name: 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
• CAS No.: 270595-83-0
• Molecular Formula: C₆₄H₆₇N₃O₁₀
• Molecular Weight: 1038.25

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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: 99.0%

benzyl bromide (100-39-0) + (2R,3S,4R,5R,6R)-6-((1S,2R,3S,4R,5S,6R)-2-Allyloxy-3,4,5,6-tetrakis-benzyloxy-cyclohexyloxy)-5-azido-2-hydroxymethyl-tetrahydro-pyran-3,4-diol → 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 (270595-83-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 1h;

DOI:10.1002/(SICI)1099-0690(200004)2000:8<1539::AID-EJOC1539>3.0.CO;2-2

Reference yield: 35.0%

1-O-Allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol (135267-01-5) + O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α/β-D-glucopyranosyl) trichloroacetimidate (220688-25-5) → 6-O-allyl-1-O-(3,4,6-tri-O-benzyl-2-azido-2-deoxy-β-D-glucopyranosyl)-2,3,4,5-tetra-O-benzyl-D-chiro-inositol + 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 (270595-83-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -25 ℃; for 0.5h;

DOI:10.1002/(SICI)1099-0690(200004)2000:8<1539::AID-EJOC1539>3.0.CO;2-2

Reference yield:

D-chiro-inositol → 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 (270595-83-0)

Guidance literature:

Multi-step reaction with 11 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

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; thiophenol; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; diethylazodicarboxylate; dmap; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 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;

DOI:10.1002/(SICI)1099-0690(200004)2000:8<1539::AID-EJOC1539>3.0.CO;2-2

upstream raw materials:

benzyl bromide

1-O-Allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol

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

2,3:4,5-tetra-O-acetyl-6-O-allyl-1-O-methoxymethyl-D-chiroinositol

Downstream raw materials:

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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