(3aS,4R,5S,6S,7R,7aR)-4-((2R,3R,4R,5S,6R)-5-Allyloxy-3-azido-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5,6,7-tris-benzyloxy-2-oxo-hexahydro-2λ⁵-benzo[1,3,2]dioxaphosphol-2-ol

Base Information

• Chemical Name: (3aS,4R,5S,6S,7R,7aR)-4-((2R,3R,4R,5S,6R)-5-Allyloxy-3-azido-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5,6,7-tris-benzyloxy-2-oxo-hexahydro-2λ⁵-benzo[1,3,2]dioxaphosphol-2-ol
• CAS No.: 452915-75-2
• Molecular Formula: C₅₀H₅₄N₃O₁₂P
• Molecular Weight: 919.965

Synonyms:

Chemical Property of (3aS,4R,5S,6S,7R,7aR)-4-((2R,3R,4R,5S,6R)-5-Allyloxy-3-azido-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5,6,7-tris-benzyloxy-2-oxo-hexahydro-2λ⁵-benzo[1,3,2]dioxaphosphol-2-ol

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Technology Process of (3aS,4R,5S,6S,7R,7aR)-4-((2R,3R,4R,5S,6R)-5-Allyloxy-3-azido-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5,6,7-tris-benzyloxy-2-oxo-hexahydro-2λ⁵-benzo[1,3,2]dioxaphosphol-2-ol

There total 2 articles about (3aS,4R,5S,6S,7R,7aR)-4-((2R,3R,4R,5S,6R)-5-Allyloxy-3-azido-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5,6,7-tris-benzyloxy-2-oxo-hexahydro-2λ⁵-benzo[1,3,2]dioxaphosphol-2-ol 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: 100.0%

6-O-(4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3,4,5-tri-O-benzyl-D-myo-inositol (452915-74-1) → (3aS,4R,5S,6S,7R,7aR)-4-((2R,3R,4R,5S,6R)-5-Allyloxy-3-azido-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5,6,7-tris-benzyloxy-2-oxo-hexahydro-2λ5-benzo[1,3,2]dioxaphosphol-2-ol (452915-75-2)

Guidance literature:

With pyridine; methyl dichlorophosphoridate; for 2h;

DOI:10.1016/S0040-4020(02)00359-9

Reference yield:

6-O-(4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3,4,5-tri-O-benzyl-1,2-O-(L-1,7,7-trimethyl[2.2.1]bicyclohept-6-ylidene)-D-myo-inositol → (3aS,4R,5S,6S,7R,7aR)-4-((2R,3R,4R,5S,6R)-5-Allyloxy-3-azido-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5,6,7-tris-benzyloxy-2-oxo-hexahydro-2λ5-benzo[1,3,2]dioxaphosphol-2-ol (452915-75-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / CF₃COOH / CHCl₃ / 16 h

2: 100 percent / methyl dichlorophosphate; pyridine / 2 h

With pyridine; trifluoroacetic acid; methyl dichlorophosphoridate; In chloroform;

DOI:10.1016/S0040-4020(02)00359-9

Reference yield:

(3aS,4R,5S,6S,7R,7aR)-4-((2R,3R,4R,5S,6R)-5-Allyloxy-3-azido-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-5,6,7-tris-benzyloxy-2-oxo-hexahydro-2λ5-benzo[1,3,2]dioxaphosphol-2-ol (452915-75-2) → 6-O-(2-Amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1,2-(Cyclic)phosphate (140391-24-8)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -33 ℃; for 0.0166667h;

DOI:10.1016/S0040-4020(02)00359-9

upstream raw materials:

6-O-(4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3,4,5-tri-O-benzyl-D-myo-inositol

Downstream raw materials:

6-O-(2-Amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1,2-(Cyclic)phosphate

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