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

Base Information

• Chemical Name: 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->1)-6-O-allyl-2,3,4,5-tetra-O-benzyl-L-chiro-inositol
• CAS No.: 637329-54-5
• Molecular Formula: C₆₄H₆₇N₃O₁₀
• Molecular Weight: 1038.25

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

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

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

There total 2 articles about 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->1)-6-O-allyl-2,3,4,5-tetra-O-benzyl-L-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: 42.0%

2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (99049-62-4) + (1R,2R,3R,4S,5S,6R)-2-Allyloxy-3,4,5,6-tetrakis-benzyloxy-cyclohexanol (638203-39-1) → 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->1)-6-O-allyl-2,3,4,5-tetra-O-benzyl-L-chiro-inositol (637329-55-6) + 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->1)-6-O-allyl-2,3,4,5-tetra-O-benzyl-L-chiro-inositol (637329-54-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -25 - 20 ℃; for 0.666667h;

DOI:10.1002/chem.200400746

Reference yield: 42.0%

1-((2S,3S,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-2,2,2-trichloro-ethylideneamine + (1R,2R,3R,4S,5S,6R)-2-Allyloxy-3,4,5,6-tetrakis-benzyloxy-cyclohexanol (638203-39-1) → 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-β-(1->1)-6-O-allyl-2,3,4,5-tetra-O-benzyl-L-chiro-inositol (637329-55-6) + 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->1)-6-O-allyl-2,3,4,5-tetra-O-benzyl-L-chiro-inositol (637329-54-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -25 - 20 ℃; for 0.666667h;

DOI:10.1055/s-2003-40339

Reference yield: 62.0%

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl-α-(1->1)-6-O-allyl-2,3,4,5-tetra-O-benzyl-L-chiro-inositol (637329-54-5) → (1S,2R,3S,4R,5S,6R)-2-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrakis-benzyloxy-cyclohexanol

Guidance literature:

With sodium acetate; palladium dichloride; In acetic acid; at 20 ℃; for 6h;

DOI:10.1055/s-2003-40339

upstream raw materials:

(1R,2R,3R,4S,5S,6R)-2-Allyloxy-3,4,5,6-tetrakis-benzyloxy-cyclohexanol

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

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