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

Base Information

• Chemical Name: 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-6-O-allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol
• CAS No.: 270595-86-3
• Molecular Formula: C₄₉H₅₅N₃O₁₃
• Molecular Weight: 893.988

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

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

There total 9 articles about 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-6-O-allyl-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: 44.0%

1-O-Allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol (135267-01-5) + 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate (145840-43-3) → 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl)-6-O-allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol + 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-6-O-allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol (270595-86-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; In dichloromethane; at 25 ℃; for 1h;

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

Reference yield:

D-chiro-inositol → 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-6-O-allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol (270595-86-3)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; 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;

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

Reference yield:

(1R,2S,3S,4R,5R,6R)-5-Allyloxy-6-methoxymethoxy-cyclohexane-1,2,3,4-tetraol → 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-6-O-allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol (270595-86-3)

Guidance literature:

Multi-step reaction with 4 steps

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

2.1: NaOMe / methanol / 0.5 h / 25 °C

2.2: 89 percent / NaH / dimethylformamide

3.1: 86 percent / PhSH; BF₃Et₂O / CH₂Cl₂ / 0.5 h / -10 °C

4.1: 44 percent / MS 4 Angstroem; TMSOTf / CH₂Cl₂ / 1 h / 25 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; boron trifluoride diethyl etherate; sodium methylate; thiophenol; In tetrahydrofuran; methanol; dichloromethane; 1.1: Acetylation / 2.1: Deacetylation / 2.2: Alkylation / 3.1: deprotection / 4.1: Etherification;

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

upstream raw materials:

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

3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranosyl trichloroacetimidate

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

1-D-1,2-anhydro-3,4:5,6-bis-O-(tetraisopropyldisiloxane-1,3-diyl)-myo-inositol

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

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

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