methyl (3S,4R,5R,6S)-3-(benzo[d][1,3]dioxol-5-yl)-4,5,6-tri(benzyloxy)-7-octenoate

Base Information

Chemical Name:methyl (3S,4R,5R,6S)-3-(benzo[d][1,3]dioxol-5-yl)-4,5,6-tri(benzyloxy)-7-octenoate
CAS No.:674325-80-5
Molecular Formula:C₃₇H₃₈O₇
Molecular Weight:594.705
Hs Code.:

Synonyms:methyl (3S,4R,5R,6S)-3-(benzo[d][1,3]dioxol-5-yl)-4,5,6-tri(benzyloxy)-7-octenoate

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Chemical Property of methyl (3S,4R,5R,6S)-3-(benzo[d][1,3]dioxol-5-yl)-4,5,6-tri(benzyloxy)-7-octenoate

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Technology Process of methyl (3S,4R,5R,6S)-3-(benzo[d][1,3]dioxol-5-yl)-4,5,6-tri(benzyloxy)-7-octenoate

There total 6 articles about methyl (3S,4R,5R,6S)-3-(benzo[d][1,3]dioxol-5-yl)-4,5,6-tri(benzyloxy)-7-octenoate 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: 95.0%

: 2635-13-4
1,2-(methylenedioxy)-4-bromobenzene

: 201603-46-5
methyl (2E,4R,5R,6S)-4,5,6-tri(benzyloxy)-2,7-octadienoate

: 674325-80-5
methyl (3S,4R,5R,6S)-3-(benzo[d][1,3]dioxol-5-yl)-4,5,6-tri(benzyloxy)-7-octenoate

Guidance literature:: 1,2-(methylenedioxy)-4-bromobenzene; With magnesium; In tetrahydrofuran;

With copper(l) iodide; In tetrahydrofuran; at 0 ℃; for 0.333333h;

methyl (2E,4R,5R,6S)-4,5,6-tri(benzyloxy)-2,7-octadienoate; With chloro-trimethyl-silane; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1021/ol049942p

Reference yield:

: 242143-00-6
methyl 2,3,4-tri-O-benzyl-D-xylopyranoside

: 674325-80-5
methyl (3S,4R,5R,6S)-3-(benzo[d][1,3]dioxol-5-yl)-4,5,6-tri(benzyloxy)-7-octenoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 71 percent / H₂SO₄ / acetic acid; dioxane

2.1: BuLi / tetrahydrofuran; pentane / 2 h / 20 °C

2.2: 80 percent / tetrahydrofuran; pentane / Heating

3.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 °C

4.1: 9.7 g / CH₂Cl₂ / -78 - 20 °C

5.1: Mg / tetrahydrofuran / Heating

5.2: CuI / tetrahydrofuran / 0.67 h / -78 °C

5.3: 95 percent / tetrahydrofuran / -78 - 20 °C

With n-butyllithium; oxalyl dichloride; sulfuric acid; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetic acid; pentane; 2.2: Wittig methylenation / 3.1: Swern oxidation;
DOI:10.1021/jo0607562

Reference yield:

: 91-09-8,612-05-5,1825-00-9,2500-78-9,3867-83-2,3945-28-6,5328-63-2,6206-67-3,6207-01-8,6207-03-0,7404-24-2,17289-61-1,18449-76-8,33509-64-7,36793-06-3,41897-31-8,41897-32-9,41897-33-0,41897-34-1,41897-37-4,41897-38-5,41897-39-6,53448-52-5,65137-86-2,89615-04-3,89615-05-4,131233-91-5,14703-09-4
methyl xyloside

: 674325-80-5
methyl (3S,4R,5R,6S)-3-(benzo[d][1,3]dioxol-5-yl)-4,5,6-tri(benzyloxy)-7-octenoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH; Bu₄NI / dimethylformamide / 0.5 h / 0 °C

2.1: 71 percent / H₂SO₄ / acetic acid; dioxane

3.1: BuLi / tetrahydrofuran; pentane / 2 h / 20 °C

3.2: 80 percent / tetrahydrofuran; pentane / Heating

4.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 °C

5.1: 9.7 g / CH₂Cl₂ / -78 - 20 °C

6.1: Mg / tetrahydrofuran / Heating

6.2: CuI / tetrahydrofuran / 0.67 h / -78 °C

6.3: 95 percent / tetrahydrofuran / -78 - 20 °C

With n-butyllithium; oxalyl dichloride; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; acetic acid; N,N-dimethyl-formamide; pentane; 3.2: Wittig methylenation / 4.1: Swern oxidation;
DOI:10.1021/jo0607562