Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• CAS No.: 114861-16-4
• Molecular Formula: C₂₅H₃₁F₃O₇SSi
• Molecular Weight: 560.664

Synonyms:Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Chemical Property of Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Chemical Property:

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Technology Process of Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

There total 5 articles about Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-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:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (114861-16-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / imidazole / pentane / 3 h / Ambient temperature

2: pyridine / CH₂Cl₂ / 0.25 h / -10 °C

With pyridine; 1H-imidazole; In dichloromethane; pentane;

DOI:10.1016/S0040-4020(98)00819-9

Reference yield:

trifluoromethylsulfonic anhydride (358-23-6) + 1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose (114861-14-2) → Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (114861-16-4)

Guidance literature:

With pyridine; In dichloromethane; for 9h; Ambient temperature;

DOI:10.1021/ja9525622

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (114861-16-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / pyridine / 18 h / Ambient temperature

2: pyridine / CH₂Cl₂ / 9 h / Ambient temperature

With pyridine; In dichloromethane;

DOI:10.1021/ja9525622

upstream raw materials:

trifluoromethylsulfonic anhydride

1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose

D-Xylose

1,2-O-isopropylidene-α-D-xylose

Downstream raw materials:

3-azido-5-O-(4-phenylbenzyl)-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

Benzoic acid (3R,4R,5S)-4-azido-2-methoxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

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