(benzyloxy)(diisopropylamino)[methyl 5-O-(2-acetoxyethyl)-3,4-di-O-acetylquinate]phosphane

Base Information

Chemical Name:(benzyloxy)(diisopropylamino)[methyl 5-O-(2-acetoxyethyl)-3,4-di-O-acetylquinate]phosphane
CAS No.:286956-46-5
Molecular Formula:C₂₉H₄₄NO₁₁P
Molecular Weight:613.642
Hs Code.:

Synonyms:(benzyloxy)(diisopropylamino)[methyl 5-O-(2-acetoxyethyl)-3,4-di-O-acetylquinate]phosphane

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Chemical Property of (benzyloxy)(diisopropylamino)[methyl 5-O-(2-acetoxyethyl)-3,4-di-O-acetylquinate]phosphane

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Technology Process of (benzyloxy)(diisopropylamino)[methyl 5-O-(2-acetoxyethyl)-3,4-di-O-acetylquinate]phosphane

There total 9 articles about (benzyloxy)(diisopropylamino)[methyl 5-O-(2-acetoxyethyl)-3,4-di-O-acetylquinate]phosphane 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: 65.0%

: 128753-68-4
(benzyloxy)chloro(diisopropylamino)phosphane

: 286956-44-3
methyl 5-O-(2-acetoxyethyl)-3,4-di-O-acetylquinate

: 286956-46-5
(benzyloxy)(diisopropylamino)[methyl 5-O-(2-acetoxyethyl)-3,4-di-O-acetylquinate]phosphane

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 18h;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

: 130021-73-7
methyl 3,4-O-cyclohexylidenequinate

: 286956-46-5
(benzyloxy)(diisopropylamino)[methyl 5-O-(2-acetoxyethyl)-3,4-di-O-acetylquinate]phosphane

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / trifluoromethanesulfonic acid / CH₂Cl₂; cyclohexane / 5 h / 0 - 20 °C

2: 82 percent / pyridine; DMAP / 14 h / 20 °C

3: O₃ / CH₂Cl₂; methanol / 0.42 h / -78 °C

4: 6.39 percent / NaBH₄ / CH₂Cl₂; methanol / 3 h / -60 - 0 °C

5: 92 percent / pyridine / ethyl acetate / 12 h

6: 100 percent / aq. AcOH / 1 h / 60 - 70 °C

7: NaOMe / methanol / 1.5 h / 20 °C

8: 205 mg / pyridine; DMAP / ethyl acetate / 12 h

9: 65 percent / diisopropylethylamine / acetonitrile / 18 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; trifluorormethanesulfonic acid; sodium methylate; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; cyclohexane; ethyl acetate; acetonitrile; 1: allylation / 2: Acetylation / 3: ozonolysis / 4: Reduction / 5: Acetylation / 6: Ring cleavage / 7: Deacetylation / 8: Acetylation / 9: Condensation;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

: (1S,3R,4R,5R)-1,3,4-Trihydroxy-5-(2-hydroxy-ethoxy)-cyclohexanecarboxylic acid methyl ester

: 286956-46-5
(benzyloxy)(diisopropylamino)[methyl 5-O-(2-acetoxyethyl)-3,4-di-O-acetylquinate]phosphane

Guidance literature:: Multi-step reaction with 2 steps

1: 205 mg / pyridine; DMAP / ethyl acetate / 12 h

2: 65 percent / diisopropylethylamine / acetonitrile / 18 h / 20 °C

With pyridine; dmap; N-ethyl-N,N-diisopropylamine; In ethyl acetate; acetonitrile; 1: Acetylation / 2: Condensation;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8