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

Base Information

• Chemical Name: (1R,2S,6S,7R,8R)-7-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-phenyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane
• CAS No.: 162710-67-0
• Molecular Formula: C₄₃H₄₆O₁₀
• Molecular Weight: 722.832

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

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

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

There total 5 articles about (1R,2S,6S,7R,8R)-7-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-phenyl-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: 83.0%

benzyl bromide (100-39-0) + O-(3-O-Allyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2,3-O-endo/exo-benzylidene-β-D-mannopyranose (162710-66-9) → (1R,2S,6S,7R,8R)-7-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-phenyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undecane (162710-67-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; 1.) r.t., 1 h, 2.) r.t., 2 h;

DOI:10.1021/jo00111a008

Reference yield:

1,6-anhydro-2,3-O-endo-benzylidene-β-mannopyranose (5349-10-0) → (1R,2S,6S,7R,8R)-7-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-phenyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undecane (162710-67-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / trimethylsilyl triflate, 4 Angstroem molecular sieves / CH₂Cl₂ / 1.) -20 deg C, 2 h, 2.) -20 deg C to 0 deg C, 2 h

2: 99 percent / NaOMe / methanol / 2 h / Ambient temperature

3: 1.) dibutyltin oxide, N-methylimidazole, 3 Angstroem molecular sieves / 1.) CH₃CN, 80 deg C, 2 h, 2.) 80 deg C, 3 h

4: 83 percent / NaH / dimethylformamide / 1.) r.t., 1 h, 2.) r.t., 2 h

With 1-methyl-1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; sodium hydride; di(n-butyl)tin oxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00111a008

Reference yield:

O-(β-D-Galactopyranosyl)-(1->4)-1,6-anhydro-2,3-O-endo/exo-benzylidene-β-D-mannopyranose (162710-65-8) → (1R,2S,6S,7R,8R)-7-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-phenyl-3,5,10,11-tetraoxa-tricyclo[6.2.1.02,6]undecane (162710-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) dibutyltin oxide, N-methylimidazole, 3 Angstroem molecular sieves / 1.) CH₃CN, 80 deg C, 2 h, 2.) 80 deg C, 3 h

2: 83 percent / NaH / dimethylformamide / 1.) r.t., 1 h, 2.) r.t., 2 h

With 1-methyl-1H-imidazole; 3 A molecular sieve; sodium hydride; di(n-butyl)tin oxide; In N,N-dimethyl-formamide;

DOI:10.1021/jo00111a008

upstream raw materials:

benzyl bromide

O-(3-O-Allyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2,3-O-endo/exo-benzylidene-β-D-mannopyranose

1,6-anhydro-2,3-O-endo-benzylidene-β-mannopyranose

O-(β-D-Galactopyranosyl)-(1->4)-1,6-anhydro-2,3-O-endo/exo-benzylidene-β-D-mannopyranose

Downstream raw materials:

O-(2,3,4-Tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-4)>-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

O-(2,3,4-Tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-4)>-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Trifluoro-methanesulfonic acid (1R,2S,3S,4S,5R)-2-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

O-(3-O-Allyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

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