methyl (3aR,4S,6S,6aR)-6-(4-iodophenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate

Base Information

Chemical Name:methyl (3aR,4S,6S,6aR)-6-(4-iodophenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate
CAS No.:1395409-46-7
Molecular Formula:C₁₅H₁₇IO₅
Molecular Weight:404.201
Hs Code.:

Synonyms:methyl (3aR,4S,6S,6aR)-6-(4-iodophenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate

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Chemical Property of methyl (3aR,4S,6S,6aR)-6-(4-iodophenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate

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Technology Process of methyl (3aR,4S,6S,6aR)-6-(4-iodophenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate

There total 5 articles about methyl (3aR,4S,6S,6aR)-6-(4-iodophenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-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:

: 1395409-44-5
(R)-1-[(3aS,4R,6S,6aR)-6-(4-iodophenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethane-1,2-diol

: 74-88-4
methyl iodide

: 1395409-46-7
methyl (3aR,4S,6S,6aR)-6-(4-iodophenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate

Guidance literature:: (R)-1-[(3aS,4R,6S,6aR)-6-(4-iodophenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]ethane-1,2-diol; With sodium periodate; In methanol; at 20 ℃; for 2h;

With silver nitrate; potassium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 0.583333h;

methyl iodide; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1016/j.ejmech.2016.01.032

Reference yield:

: 67-56-1
methanol

: C₁₄H₁₅IO₅

: 1395409-46-7
methyl (3aR,4S,6S,6aR)-6-(4-iodophenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate

: 1395409-48-9
methyl (2S,3R,4S,5S)-3,4-dihydroxy-5-(4-iodophenyl)-2,3,4,5-tetrahydrofuran-2-carboxylate

Guidance literature:: With toluene-4-sulfonic acid; for 16h; Reflux;
DOI:10.1039/c3ob41082j

Reference yield:

: 7306-64-1,14440-56-3,23262-80-8,27108-15-2,49561-21-9,67642-42-6
2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone

: 1395409-46-7
methyl (3aR,4S,6S,6aR)-6-(4-iodophenyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / -78 °C

2.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 1 h / -40 °C / Inert atmosphere

2.2: 16 h / 20 °C

3.1: sodium periodate / methanol / 2 h / 20 °C

3.2: 0.58 h / 20 °C

3.3: 20 °C

With triethylsilane; sodium periodate; boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; acetonitrile;
DOI:10.1016/j.ejmech.2016.01.032