(1S,2S,4R,5S)-4-((R)-1-carboxy-2-phenyl-ethoxy)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

Base Information

Chemical Name:(1S,2S,4R,5S)-4-((R)-1-carboxy-2-phenyl-ethoxy)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester
CAS No.:934482-19-6
Molecular Formula:C₃₉H₅₄O₁₇
Molecular Weight:794.848
Hs Code.:

Synonyms:(1S,2S,4R,5S)-4-((R)-1-carboxy-2-phenyl-ethoxy)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

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Chemical Property of (1S,2S,4R,5S)-4-((R)-1-carboxy-2-phenyl-ethoxy)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

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Technology Process of (1S,2S,4R,5S)-4-((R)-1-carboxy-2-phenyl-ethoxy)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

There total 3 articles about (1S,2S,4R,5S)-4-((R)-1-carboxy-2-phenyl-ethoxy)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl 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: 70.0%

: 934482-15-2
(1S,2S,4R,5S)-4-((R)-1-benzyloxycarbonyl-2-phenyl-ethoxy)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

: 934482-19-6
(1S,2S,4R,5S)-4-((R)-1-carboxy-2-phenyl-ethoxy)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; water; at 20 ℃;
DOI:10.1021/ja066633g

Reference yield:

: 7622-21-1
benzyl-(S)-(-)-2-hydroxy-3-phenylpropionate

: 934482-19-6
(1S,2S,4R,5S)-4-((R)-1-carboxy-2-phenyl-ethoxy)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / lutidine / CH₂Cl₂ / 0.33 h / 20 °C

2.1: dibutyltin oxide / benzene

2.2: CsF / 1,2-dimethoxy-ethane

3.1: 45 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂ / 3 h / -30 °C

4.1: 70 percent / H₂ / Pd/C / methanol; H₂O / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; lutidine; hydrogen; di(n-butyl)tin oxide; palladium on activated charcoal; In methanol; dichloromethane; water; benzene;
DOI:10.1021/ja066633g

Reference yield:

: 146953-71-1
(S)-3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid benzyl ester

: 934482-19-6
(1S,2S,4R,5S)-4-((R)-1-carboxy-2-phenyl-ethoxy)-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: dibutyltin oxide / benzene

1.2: CsF / 1,2-dimethoxy-ethane

2.1: 45 percent / molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂ / 3 h / -30 °C

3.1: 70 percent / H₂ / Pd/C / methanol; H₂O / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; di(n-butyl)tin oxide; palladium on activated charcoal; In methanol; dichloromethane; water; benzene;
DOI:10.1021/ja066633g