2-(2-Benzyloxy-ethyl)-2-((2R,3S)-3-iodomethyl-oxiranylmethyl)-[1,3]dioxolane

Base Information

Chemical Name:2-(2-Benzyloxy-ethyl)-2-((2R,3S)-3-iodomethyl-oxiranylmethyl)-[1,3]dioxolane
CAS No.:362624-05-3
Molecular Formula:C₁₆H₂₁IO₄
Molecular Weight:404.245
Hs Code.:

Synonyms:2-(2-Benzyloxy-ethyl)-2-((2R,3S)-3-iodomethyl-oxiranylmethyl)-[1,3]dioxolane

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Chemical Property of 2-(2-Benzyloxy-ethyl)-2-((2R,3S)-3-iodomethyl-oxiranylmethyl)-[1,3]dioxolane

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Technology Process of 2-(2-Benzyloxy-ethyl)-2-((2R,3S)-3-iodomethyl-oxiranylmethyl)-[1,3]dioxolane

There total 8 articles about 2-(2-Benzyloxy-ethyl)-2-((2R,3S)-3-iodomethyl-oxiranylmethyl)-[1,3]dioxolane 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: 90.0%

: 362624-04-2
{(2R,3R)-3-[2-(2-Benzyloxy-ethyl)-[1,3]dioxolan-2-ylmethyl]-oxiranyl}-methanol

: 362624-05-3
2-(2-Benzyloxy-ethyl)-2-((2R,3S)-3-iodomethyl-oxiranylmethyl)-[1,3]dioxolane

Guidance literature:: With 1H-imidazole; iodine; thiamine diphosphate; In diethyl ether; acetonitrile; at 20 ℃;
DOI:10.1016/S0040-4039(01)00841-3

Reference yield:

: 5694-95-1
2-(2-(2-hydroxyethyl)-1,3-dioxolan-2-yl)ethanol

: 362624-05-3
2-(2-Benzyloxy-ethyl)-2-((2R,3S)-3-iodomethyl-oxiranylmethyl)-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / NaH / tetrahydrofuran / 0 °C

2: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 0 °C

3: CH₂Cl₂

4: 85 percent / DIBAL-H / CH₂Cl₂ / -78 °C

5: 82 percent / D(-)DIPT; TBHP / Ti(O-i-Pr)4 / CH₂Cl₂ / 9 h / -20 °C

6: 90 percent / TPP; I₂; imidazole / diethyl ether; acetonitrile / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; oxalyl dichloride; iodine; thiamine diphosphate; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; titanium(IV) isopropylate; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; 2: Swern oxidation / 3: Wittig olefination / 5: Sharpless asymmetric epoxidation;
DOI:10.1016/S0040-4039(01)00841-3

Reference yield:

: 6506-31-6
dimethyl acetonedicarboxylate ethylene ketal

: 362624-05-3
2-(2-Benzyloxy-ethyl)-2-((2R,3S)-3-iodomethyl-oxiranylmethyl)-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / LiAlH₄ / tetrahydrofuran / Heating

2: 75 percent / NaH / tetrahydrofuran / 0 °C

3: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 0 °C

4: CH₂Cl₂

5: 85 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6: 82 percent / D(-)DIPT; TBHP / Ti(O-i-Pr)4 / CH₂Cl₂ / 9 h / -20 °C

7: 90 percent / TPP; I₂; imidazole / diethyl ether; acetonitrile / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; lithium aluminium tetrahydride; oxalyl dichloride; iodine; thiamine diphosphate; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; titanium(IV) isopropylate; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; 3: Swern oxidation / 4: Wittig olefination / 6: Sharpless asymmetric epoxidation;
DOI:10.1016/S0040-4039(01)00841-3