(1R,2R)-methyl 4-(2-methylallyl)-2-oxo-tetrahydro-2H-pyran-3-carbonylcarbamate

Base Information

Chemical Name:(1R,2R)-methyl 4-(2-methylallyl)-2-oxo-tetrahydro-2H-pyran-3-carbonylcarbamate
CAS No.:1421739-29-8
Molecular Formula:C₁₃H₁₉NO₄
Molecular Weight:253.298
Hs Code.:

Synonyms:(1R,2R)-methyl 4-(2-methylallyl)-2-oxo-tetrahydro-2H-pyran-3-carbonylcarbamate

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Chemical Property of (1R,2R)-methyl 4-(2-methylallyl)-2-oxo-tetrahydro-2H-pyran-3-carbonylcarbamate

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Technology Process of (1R,2R)-methyl 4-(2-methylallyl)-2-oxo-tetrahydro-2H-pyran-3-carbonylcarbamate

There total 3 articles about (1R,2R)-methyl 4-(2-methylallyl)-2-oxo-tetrahydro-2H-pyran-3-carbonylcarbamate 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%

: 18292-38-1
2-methallyltrimethylsilane

: 1421739-42-5
methyl 6-oxocyclohex-1-enecarbonylcarbamate

: 1421739-29-8
(1R,2R)-methyl 4-(2-methylallyl)-2-oxo-tetrahydro-2H-pyran-3-carbonylcarbamate

Guidance literature:: methyl 6-oxocyclohex-1-enecarbonylcarbamate; With C₁₇H₂₈CuF₆N₄O₁₂S₄; In dichloromethane; at 20 ℃; for 0.0833333h; Inert atmosphere;

2-methallyltrimethylsilane; In dichloromethane; at -30 ℃; for 10.5h; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ol303381c

Reference yield:

: C₁₀H₁₃NO₄

: 1421739-29-8
(1R,2R)-methyl 4-(2-methylallyl)-2-oxo-tetrahydro-2H-pyran-3-carbonylcarbamate

Guidance literature:: Multi-step reaction with 2 steps

1.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 12 h / 0 - 20 °C / Inert atmosphere

2.1: C₁₇H₂₈CuF₆N₄O₁₂S₄ / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

2.2: 10.5 h / -30 °C / Inert atmosphere

With chloro-trimethyl-silane; C₁₇H₂₈CuF₆N₄O₁₂S₄; sodium iodide; In dichloromethane; acetonitrile; 2.2: |Hosomi-Sakurai Reaction;
DOI:10.1021/ol303381c

Reference yield:

: 18292-38-1
2-methallyltrimethylsilane

: 1421739-42-5
methyl 6-oxocyclohex-1-enecarbonylcarbamate

: 1421739-29-8
(1R,2R)-methyl 4-(2-methylallyl)-2-oxo-tetrahydro-2H-pyran-3-carbonylcarbamate

: 1421739-28-7
(1S,2S)-methyl 4-(2-methylallyl)-2-oxo-tetrahydro-2H-pyran-3-carbonylcarbamate

Guidance literature:: With C₁₇H₂₆CuF₆N₂O₈S₂; In dichloromethane; at -30 ℃; for 36h; Overall yield = 93 %; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ol303381c