Benzoic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 860640-02-4
• Molecular Formula: C₃₁H₂₈F₃NO₉S₂
• Molecular Weight: 679.692
• Mol file: 860640-02-4.mol

Synonyms:Benzoic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Benzoic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester

There total 5 articles about Benzoic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-trifluoromethanesulfonyloxy-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:

ethyl 6-O-benzoyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (860639-92-5) + trifluoromethylsulfonic anhydride (358-23-6) → Benzoic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester (860640-02-4)

Guidance literature:

With pyridine; In dichloromethane; at -5 - 20 ℃;

DOI:10.1081/CAR-200061584

Reference yield:

Benzoic acid (2R,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-oxo-tetrahydro-pyran-2-ylmethyl ester (860640-08-0) → Benzoic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester (860640-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄; n-Bu₄NBH₄ / tetrahydrofuran / 0.17 h / -10 °C

2: pyridine / CH₂Cl₂ / -5 - 20 °C

With pyridine; sodium tetrahydroborate; tetrabutylammonium borohydride; In tetrahydrofuran; dichloromethane;

DOI:10.1081/CAR-200061584

Reference yield:

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside (99409-33-3) → Benzoic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-ylmethyl ester (860640-02-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 84 percent / NaH / dimethylformamide

2.1: ethylene glycol; trifluoroacetic acid / CH₂Cl₂ / 1 h

2.2: 84 percent / pyridine / 2 h / 0 °C

3.1: pyridine / CH₂Cl₂ / -5 - 20 °C

With pyridine; sodium hydride; ethylene glycol; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1081/CAR-200061584

upstream raw materials:

ethyl 6-O-benzoyl-3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

trifluoromethylsulfonic anhydride

Benzoic acid (2R,4R,5R,6S)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-3-oxo-tetrahydro-pyran-2-ylmethyl ester

ethyl 4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-Dglucopyranoside