(4S,6S)-4-[(1R)-2-benzyloxy-1-methyl-ethyl]-6-[(E)-propenyl]-[1,3]dioxan-2-one

Base Information

Chemical Name:(4S,6S)-4-[(1R)-2-benzyloxy-1-methyl-ethyl]-6-[(E)-propenyl]-[1,3]dioxan-2-one
CAS No.:275818-53-6
Molecular Formula:C₁₇H₂₂O₄
Molecular Weight:290.359
Hs Code.:

Synonyms:(4S,6S)-4-[(1R)-2-benzyloxy-1-methyl-ethyl]-6-[(E)-propenyl]-[1,3]dioxan-2-one

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Chemical Property of (4S,6S)-4-[(1R)-2-benzyloxy-1-methyl-ethyl]-6-[(E)-propenyl]-[1,3]dioxan-2-one

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Technology Process of (4S,6S)-4-[(1R)-2-benzyloxy-1-methyl-ethyl]-6-[(E)-propenyl]-[1,3]dioxan-2-one

There total 3 articles about (4S,6S)-4-[(1R)-2-benzyloxy-1-methyl-ethyl]-6-[(E)-propenyl]-[1,3]dioxan-2-one 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: 77.0%

: 32315-10-9
bis(trichloromethyl) carbonate

: 240485-11-4
(E)-(4S,6S,7R)-8-benzyloxy-7-methyl-oct-2-ene-4,6-diol

: 275818-53-6
(4S,6S)-4-[(1R)-2-benzyloxy-1-methyl-ethyl]-6-[(E)-propenyl]-[1,3]dioxan-2-one

Guidance literature:: With pyridine; 4 A molecular sieve; triethylamine; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1016/S0040-4020(02)00049-2

Reference yield:

: 82167-79-1
(-)-(R)-4-benzyloxy-3-methylbutan-2-one

: 275818-53-6
(4S,6S)-4-[(1R)-2-benzyloxy-1-methyl-ethyl]-6-[(E)-propenyl]-[1,3]dioxan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: (+)-Ipc₂BCl; Et₃N / diethyl ether / 2 h / 0 °C

1.2: diethyl ether / -78 °C

1.3: 95 percent / aq. H₂O₂ / diethyl ether; methanol / 1 h / 20 °C / pH 7

2.1: 91 percent / Me₄NBH(OAc)3; acetic acid / acetonitrile / 18 h / -35 °C

3.1: 77 percent / pyridine; Et₃N; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; (+)-β-chlorodiisopinocampheylborane; 4 A molecular sieve; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In diethyl ether; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4020(02)00049-2

Reference yield:

: 240485-07-8
(E)-(2R,5S)-1-benzyloxy-5-hydroxy-2-methyl-oct-6-en-3-one

: 275818-53-6
(4S,6S)-4-[(1R)-2-benzyloxy-1-methyl-ethyl]-6-[(E)-propenyl]-[1,3]dioxan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / Me₄NBH(OAc)3; acetic acid / acetonitrile / 18 h / -35 °C

2: 77 percent / pyridine; Et₃N; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; 4 A molecular sieve; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetonitrile;
DOI:10.1016/S0040-4020(02)00049-2