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

Base Information

Chemical Name:(3S,4R,5R,6S)-3-(benzo[d][1,3]dioxol-5-yl)-4,5,6-tri(benzyloxy)-7-octen-1-ol
CAS No.:674326-12-6
Molecular Formula:C₃₆H₃₈O₆
Molecular Weight:566.694
Hs Code.:

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

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

Chemical Property:

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

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

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

: 674326-12-6
(3S,4R,5R,6S)-3-(benzo[d][1,3]dioxol-5-yl)-4,5,6-tri(benzyloxy)-7-octen-1-ol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20 ℃; for 3h;
DOI:10.1021/ol049942p DOI:10.1021/jo0607562

Reference yield:

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

: 674326-12-6
(3S,4R,5R,6S)-3-(benzo[d][1,3]dioxol-5-yl)-4,5,6-tri(benzyloxy)-7-octen-1-ol

Guidance literature:: Multi-step reaction with 6 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

6.1: LiAlH₄ / diethyl ether / 3 h / 0 - 20 °C

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

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
D-Xylose

: 674326-12-6
(3S,4R,5R,6S)-3-(benzo[d][1,3]dioxol-5-yl)-4,5,6-tri(benzyloxy)-7-octen-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: SOCl₂ / 4 h / Heating

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

3.1: 71 percent / H₂SO₄ / acetic acid; dioxane

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

4.2: 80 percent / tetrahydrofuran; pentane / Heating

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

6.1: 9.7 g / CH₂Cl₂ / -78 - 20 °C

7.1: Mg / tetrahydrofuran / Heating

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

7.3: 95 percent / tetrahydrofuran / -78 - 20 °C

8.1: LiAlH₄ / diethyl ether / 3 h / 0 - 20 °C

With lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; oxalyl dichloride; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; pentane; 4.2: Wittig methylenation / 5.1: Swern oxidation;
DOI:10.1021/jo0607562