(3aR,5S,6R,6aR)-methyl 2,2-dimethyl-6-(tosyloxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate

Base Information

Chemical Name:(3aR,5S,6R,6aR)-methyl 2,2-dimethyl-6-(tosyloxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate
CAS No.:85950-36-3
Molecular Formula:C₁₆H₂₀O₈S
Molecular Weight:372.396
Hs Code.:

Synonyms:(3aR,5S,6R,6aR)-methyl 2,2-dimethyl-6-(tosyloxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate

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Chemical Property of (3aR,5S,6R,6aR)-methyl 2,2-dimethyl-6-(tosyloxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate

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Technology Process of (3aR,5S,6R,6aR)-methyl 2,2-dimethyl-6-(tosyloxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate

There total 7 articles about (3aR,5S,6R,6aR)-methyl 2,2-dimethyl-6-(tosyloxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate 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: 96.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 85950-35-2
1,2-O-isopropylidene-3-O-toluene-p-sulphonyl-α-D-xylofuranuronic acid

: 85950-36-3
(3aR,5S,6R,6aR)-methyl 2,2-dimethyl-6-(tosyloxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate

Guidance literature:: In diethyl ether; dichloromethane; at 0 ℃; for 0.333333h;
DOI:10.1007/s00726-016-2346-5

Reference yield: 88.0%

: 85950-35-2
1,2-O-isopropylidene-3-O-toluene-p-sulphonyl-α-D-xylofuranuronic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 85950-36-3
(3aR,5S,6R,6aR)-methyl 2,2-dimethyl-6-(tosyloxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate

Guidance literature:: In methanol; hexanes; diethyl ether; at 0 ℃; for 0.5h; Inert atmosphere;
DOI:10.1016/j.bmc.2011.07.022

Reference yield:

: 3253-75-6
1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside

: 85950-36-3
(3aR,5S,6R,6aR)-methyl 2,2-dimethyl-6-(tosyloxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: acetic acid / 48 h / 20 °C

2: sodium periodate / methanol; water / 24 h / 0 - 20 °C

3: acetic acid; potassium permanganate / water / 60 h / 0 - 12 °C

4: diethyl ether; dichloromethane / 0.33 h / 0 °C

With potassium permanganate; sodium periodate; acetic acid; In methanol; diethyl ether; dichloromethane; water;
DOI:10.1007/s00726-016-2346-5