2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethoxy-benzoic acid cyanomethyl ester

Base Information

Chemical Name:2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethoxy-benzoic acid cyanomethyl ester
CAS No.:674335-93-4
Molecular Formula:C₂₉H₃₅NO₇
Molecular Weight:509.599
Hs Code.:

Synonyms:2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethoxy-benzoic acid cyanomethyl ester

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Chemical Property of 2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethoxy-benzoic acid cyanomethyl ester

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Technology Process of 2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethoxy-benzoic acid cyanomethyl ester

There total 15 articles about 2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethoxy-benzoic acid cyanomethyl ester 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%

: 107-30-2
chloromethyl methyl ether

: 674336-21-1
2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid cyanomethyl ester

: 674335-93-4
2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethoxy-benzoic acid cyanomethyl ester

Guidance literature:: With sodium hydroxide; tetra-(n-butyl)ammonium iodide; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1021/ja037957x

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 674335-93-4
2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethoxy-benzoic acid cyanomethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 93 percent / TfOH / diethyl ether / 4 h / 20 °C

2.1: 95 percent / HCl / methanol / 0.17 h / 20 °C

3.1: 93 percent / PCC / CH₂Cl₂ / 4 h

4.1: LHMDS / tetrahydrofuran / -78 - 25 °C

4.2: tetrahydrofuran / 18 h / -78 - 25 °C

5.1: 1.19 g / Hg(OAc)2; aq. KI / tetrahydrofuran; H₂O / 0.5 h

6.1: 75 percent / diethyl ether / 4 h / -78 °C

7.1: 95 percent / aq. LiOH*H₂O / methanol; tetrahydrofuran / 6 h / Heating

8.1: 80 percent / Et₃N / acetone / 48 h / 52 °C

9.1: 90 percent / Bu₄NI; aq. NaOH / CH₂Cl₂ / 3 h / 20 °C

With hydrogenchloride; lithium hydroxide; sodium hydroxide; trifluorormethanesulfonic acid; mercury(II) diacetate; tetra-(n-butyl)ammonium iodide; triethylamine; pyridinium chlorochromate; potassium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;
DOI:10.1021/ja037957x

Reference yield:

: 674336-06-2
2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-hydroxy-benzoic acid

: 674335-93-4
2-[(2S,4R,6S)-4-Benzyloxy-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-2-ylmethyl]-6-methoxymethoxy-benzoic acid cyanomethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / Et₃N / acetone / 48 h / 52 °C

2: 90 percent / Bu₄NI; aq. NaOH / CH₂Cl₂ / 3 h / 20 °C

With sodium hydroxide; tetra-(n-butyl)ammonium iodide; triethylamine; In dichloromethane; acetone;
DOI:10.1021/ja037957x