Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester
• CAS No.: 860640-05-7
• Molecular Formula: C₂₇H₂₈F₃NO₈S₂
• Molecular Weight: 615.648
• Mol file: 860640-05-7.mol

Synonyms:Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester

Chemical Property of Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester

There total 6 articles about Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yl 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:

trifluoromethylsulfonic anhydride (358-23-6) + ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (419549-63-6) → Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester (860640-05-7)

Guidance literature:

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

DOI:10.1081/CAR-200061584

Reference yield:

2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (129519-28-4) → Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester (860640-05-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / NaH / tetrahydrofuran

2: 85 percent / BH₃*Me₃N; 4 Angstroem molecular sieves; AlCl₃ / tetrahydrofuran / 6 h / 20 °C

3: pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

Reference yield:

ethyl 3-O-allyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (419549-62-5) → Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester (860640-05-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / BH₃*Me₃N; 4 Angstroem molecular sieves; AlCl₃ / tetrahydrofuran / 6 h / 20 °C

2: pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; In tetrahydrofuran; dichloromethane;

DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

upstream raw materials:

trifluoromethylsulfonic anhydride

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

2-((2S,3R,4R,6R)-4-Allyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-oxo-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

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

Downstream raw materials:

ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

ethyl (3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl (3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->4)-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl (3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside