Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester
CAS No.:173655-37-3
Molecular Formula:C₅₆H₆₀O₁₁
Molecular Weight:909.086
Hs Code.:

Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester

There total 13 articles about Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester 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:

: 100-39-0
benzyl bromide

: 173655-37-3
Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / NaH / dimethylformamide

2: 70 percent / AcOH, H₂₀ / dioxane

3: 1.) Bu₂SnO, 2.) CsF / 1.) PhH, refluxed, 2.) DMF, r.t., 15 h

4: methyl sulfenyl bromide, molecular sieves 4 Angstroem / CH₂Cl₂ / Ambient temperature

With methylsulfenyl bromide; 4 A molecular sieve; water; sodium hydride; di(n-butyl)tin oxide; acetic acid; cesium fluoride; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)77648-9

Reference yield:

: 53270-14-7
benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

: 173655-37-3
Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / NaH / dimethylformamide

2: 70 percent / AcOH, H₂₀ / dioxane

3: 1.) Bu₂SnO, 2.) CsF / 1.) PhH, refluxed, 2.) DMF, r.t., 15 h

4: methyl sulfenyl bromide, molecular sieves 4 Angstroem / CH₂Cl₂ / Ambient temperature

With methylsulfenyl bromide; 4 A molecular sieve; water; sodium hydride; di(n-butyl)tin oxide; acetic acid; cesium fluoride; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)77648-9

Reference yield:

: 3359-35-1,16741-29-0,71731-74-3,78120-06-6,84911-79-5,84911-80-8,87598-99-0,87599-00-6,88818-92-2,97133-57-8,114298-06-5,127000-09-3
(2R,3R,4R,5R,6S)-2-benzyloxy-tetrahydro-6-methyl-2H-pyran-3,4,5-triol

: 173655-37-3
Acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((3R,4R,5S,6S)-2,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / p-TsOH / acetone

2: 76 percent / NaH / dimethylformamide

3: 70 percent / AcOH, H₂₀ / dioxane

4: 1.) Bu₂SnO, 2.) CsF / 1.) PhH, refluxed, 2.) DMF, r.t., 15 h

5: methyl sulfenyl bromide, molecular sieves 4 Angstroem / CH₂Cl₂ / Ambient temperature

With methylsulfenyl bromide; 4 A molecular sieve; water; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; cesium fluoride; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4039(00)77648-9