(Z)-(3S,4R)-3-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-oct-6-en-4-ol

Base Information

Chemical Name:(Z)-(3S,4R)-3-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-oct-6-en-4-ol
CAS No.:333788-68-4
Molecular Formula:C₂₆H₃₄O₅
Molecular Weight:426.553
Hs Code.:

Synonyms:(Z)-(3S,4R)-3-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-oct-6-en-4-ol

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Chemical Property of (Z)-(3S,4R)-3-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-oct-6-en-4-ol

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Technology Process of (Z)-(3S,4R)-3-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-oct-6-en-4-ol

There total 15 articles about (Z)-(3S,4R)-3-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-oct-6-en-4-ol 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: 91.0%

: 333788-83-3
Methanesulfonic acid (Z)-(1R,6R,7S)-7-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-ethyl]-non-3-enyl ester

: 333788-68-4
(Z)-(3S,4R)-3-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-oct-6-en-4-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃;
DOI:10.1016/S0040-4039(00)02281-4

Reference yield:

: 131446-96-3
(S)-2-(benzyloxy)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate

: 333788-68-4
(Z)-(3S,4R)-3-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-oct-6-en-4-ol

Guidance literature:: Multi-step reaction with 11 steps

1: 93 percent / diethyl ether / -65 - 0 °C

2: 97 percent / PPTS / ethanol / 80 °C

3: 100 percent / TEA; DMAP / CH₂Cl₂ / 60 °C

4: 98 percent / TEA; DMAP / CH₂Cl₂

5: 96 percent / TBAF / tetrahydrofuran

6: 93 percent / EDA / dimethylsulfoxide / 0 °C

7: 98 percent / AgNO₃; pyridine / acetonitrile

8: 78 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

9: 99 percent / H₂; quinoline / Lindlar cat. / methanol

10: 98 percent / TEA; DMAP / CH₂Cl₂

11: 91 percent / TBAF / tetrahydrofuran / 50 °C

With pyridine; quinoline; diazoacetic acid ethyl ester; dmap; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; silver nitrate; Lindlar catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile; 8: Yamaguchi coupling reaction;
DOI:10.1016/S0040-4039(00)02281-4

Reference yield:

: 84379-53-3
2-O-benzyl-3,4-O-isopropylidene-L-threitol

: 333788-68-4
(Z)-(3S,4R)-3-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-oct-6-en-4-ol

Guidance literature:: Multi-step reaction with 12 steps

1: 100 percent / TEA; DMAP / CH₂Cl₂

2: 93 percent / diethyl ether / -65 - 0 °C

3: 97 percent / PPTS / ethanol / 80 °C

4: 100 percent / TEA; DMAP / CH₂Cl₂ / 60 °C

5: 98 percent / TEA; DMAP / CH₂Cl₂

6: 96 percent / TBAF / tetrahydrofuran

7: 93 percent / EDA / dimethylsulfoxide / 0 °C

8: 98 percent / AgNO₃; pyridine / acetonitrile

9: 78 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

10: 99 percent / H₂; quinoline / Lindlar cat. / methanol

11: 98 percent / TEA; DMAP / CH₂Cl₂

12: 91 percent / TBAF / tetrahydrofuran / 50 °C

With pyridine; quinoline; diazoacetic acid ethyl ester; dmap; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; silver nitrate; Lindlar catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile; 9: Yamaguchi coupling reaction;
DOI:10.1016/S0040-4039(00)02281-4