(1R,2S,6S,7R,8R)-4,4-Dimethyl-7-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane

Base Information

• Chemical Name: (1R,2S,6S,7R,8R)-4,4-Dimethyl-7-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane
• CAS No.: 74808-12-1
• Molecular Formula: C₄₃H₄₈O₁₀
• Molecular Weight: 724.848

Synonyms:

Chemical Property of (1R,2S,6S,7R,8R)-4,4-Dimethyl-7-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane

Chemical Property:

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Useful:

Technology Process of (1R,2S,6S,7R,8R)-4,4-Dimethyl-7-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane

There total 2 articles about (1R,2S,6S,7R,8R)-4,4-Dimethyl-7-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane 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:

1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose (14440-51-8) + 2,2,N-Tris-(4-chloro-phenyl)-acetimidic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (74808-07-4) → (1R,2S,6S,7R,8R)-4,4-Dimethyl-7-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undecane (74808-14-3) + (1R,2S,6S,7R,8R)-4,4-Dimethyl-7-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undecane (74808-12-1)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 18h; Yield given. Yields of byproduct given;

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → (1R,2S,6S,7R,8R)-4,4-Dimethyl-7-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undecane (74808-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / NaH / CH₂Cl₂ / 5 h / Ambient temperature

2: TsOH / CH₂Cl₂ / 18 h / 20 °C

With sodium hydride; toluene-4-sulfonic acid; In dichloromethane;

upstream raw materials:

1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose

2,2,N-Tris-(4-chloro-phenyl)-acetimidic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

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