1,3,4,5-tetra-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

Base Information

• Chemical Name: 1,3,4,5-tetra-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol
• CAS No.: 297747-10-5
• Molecular Formula: C₆₈H₆₈O₁₂
• Molecular Weight: 1077.28

Synonyms:1,3,4,5-tetra-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

Chemical Property of 1,3,4,5-tetra-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

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Technology Process of 1,3,4,5-tetra-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

There total 2 articles about 1,3,4,5-tetra-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-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: 73.0%

1,3,4,5-Tetra-O-benzyl-D-myo-inositol (261722-84-3) + 3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (125392-62-3) → 1,3,4,5-tetra-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol (297747-10-5)

Guidance literature:

With N-iodo-succinimide; t-butyldimethylsiyl triflate; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1021/ol0001214

Reference yield: 39.0%

1,3,4,5-Tetra-O-benzyl-D-myo-inositol (261722-84-3) + 3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (125392-62-3) + tert-Butyl-diphenyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane (273934-59-1) → 1,3,4,5-tetra-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol (297747-10-5) + 1,3,4,5-tetra-O-benzyl-2-O-(2,3,4-tri-O-benzyl-6-O-[tert-butyldiphenylsilyl]-α-D-mannopyranosyl)-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol

Guidance literature:

With N-iodo-succinimide; t-butyldimethylsiyl triflate; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1021/ol0001214

Reference yield: 83.0%

acetic anhydride (108-24-7) + 1,3,4,5-tetra-O-benzyl-6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-D-myo-inositol (297747-10-5) → Benzoic acid (2R,3S,4S,5R,6R)-2-((1R,2S,3R,4R,5S,6S)-3-acetoxy-2,4,5,6-tetrakis-benzyloxy-cyclohexyloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:

With pyridine; dmap; at 20 ℃; for 1h;

DOI:10.1021/ol0001214

upstream raw materials:

1,3,4,5-Tetra-O-benzyl-D-myo-inositol

3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)

tert-Butyl-diphenyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane

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