(1S,2S,4S,5S,6R)-2-methoxy-6-(methoxymethyl)oxy-4-{[(4'-methoxyphenyl)methoxy]oxy}methyl-3-oxabicyclo[3.3.0]octane

Base Information

Chemical Name:(1S,2S,4S,5S,6R)-2-methoxy-6-(methoxymethyl)oxy-4-{[(4'-methoxyphenyl)methoxy]oxy}methyl-3-oxabicyclo[3.3.0]octane
CAS No.:313218-67-6
Molecular Formula:C₁₉H₂₈O₆
Molecular Weight:352.428
Hs Code.:

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Chemical Property of (1S,2S,4S,5S,6R)-2-methoxy-6-(methoxymethyl)oxy-4-{[(4'-methoxyphenyl)methoxy]oxy}methyl-3-oxabicyclo[3.3.0]octane

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Technology Process of (1S,2S,4S,5S,6R)-2-methoxy-6-(methoxymethyl)oxy-4-{[(4'-methoxyphenyl)methoxy]oxy}methyl-3-oxabicyclo[3.3.0]octane

There total 16 articles about (1S,2S,4S,5S,6R)-2-methoxy-6-(methoxymethyl)oxy-4-{[(4'-methoxyphenyl)methoxy]oxy}methyl-3-oxabicyclo[3.3.0]octane 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:

: 203248-41-3
{(2R,3R)-3-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-propyl]-oxiranyl}-methanol

: 313218-67-6
(1S,2S,4S,5S,6R)-2-methoxy-6-(methoxymethyl)oxy-4-{[(4'-methoxyphenyl)methoxy]oxy}methyl-3-oxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 9 steps

1.1: 95 percent / NaH / tetrahydrofuran; dimethylformamide / 1 h / 0 °C

2.1: TBAF / tetrahydrofuran / 1 h / 20 °C

3.1: 3.89 g / DMAP / CH₂Cl₂ / 0.25 h / 0 °C

4.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 99 percent / tetrahydrofuran / -78 - 20 °C

5.1: OsO₄; NaIO₄ / dioxane; H₂O / 24 h

6.1: 2.40 g / Jones reagent / acetone / 0.17 h / 0 °C

7.1: 91 percent / NaH₂PO₄; Na-Hg / methanol / 0.5 h / 20 °C

8.1: DIBAL-H / toluene; hexane / 1 h / -78 °C

9.1: 1.66 g / PPTS / 3 h / 20 °C

With dmap; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; jones reagent; sodium amalgam; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 1.1: Alkylation / 2.1: desilylation / 3.1: mesylation / 4.1: Metallation / 4.2: Cyclization / 5.1: Oxidation / 6.1: Oxidation / 7.1: Reduction / 8.1: Reduction / 9.1: Methylation;
DOI:10.1016/S0040-4020(00)00730-4

Reference yield:

: 203248-26-4
(E)-(R)-6-(tert-butyldimethylsilyl)oxy-4-(methoxymethyl)oxy-2-hexen-1-ol

: 313218-67-6
(1S,2S,4S,5S,6R)-2-methoxy-6-(methoxymethyl)oxy-4-{[(4'-methoxyphenyl)methoxy]oxy}methyl-3-oxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 10 steps

1.1: 89 percent / Ti(OPr-i)4; D-(-)-diethyl tartrate; TBHP / CH₂Cl₂ / 5 h / -20 °C

2.1: 95 percent / NaH / tetrahydrofuran; dimethylformamide / 1 h / 0 °C

3.1: TBAF / tetrahydrofuran / 1 h / 20 °C

4.1: 3.89 g / DMAP / CH₂Cl₂ / 0.25 h / 0 °C

5.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 99 percent / tetrahydrofuran / -78 - 20 °C

6.1: OsO₄; NaIO₄ / dioxane; H₂O / 24 h

7.1: 2.40 g / Jones reagent / acetone / 0.17 h / 0 °C

8.1: 91 percent / NaH₂PO₄; Na-Hg / methanol / 0.5 h / 20 °C

9.1: DIBAL-H / toluene; hexane / 1 h / -78 °C

10.1: 1.66 g / PPTS / 3 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; jones reagent; sodium amalgam; diethyl (2S,3S)-tartrate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 1.1: Epoxidation / 2.1: Alkylation / 3.1: desilylation / 4.1: mesylation / 5.1: Metallation / 5.2: Cyclization / 6.1: Oxidation / 7.1: Oxidation / 8.1: Reduction / 9.1: Reduction / 10.1: Methylation;
DOI:10.1016/S0040-4020(00)00730-4

Reference yield:

: 313218-76-7
(R)-3-[(2R,3R)-3-(4-Methoxy-benzyloxymethyl)-oxiranyl]-3-methoxymethoxy-propan-1-ol

: 313218-67-6
(1S,2S,4S,5S,6R)-2-methoxy-6-(methoxymethyl)oxy-4-{[(4'-methoxyphenyl)methoxy]oxy}methyl-3-oxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 7 steps

1.1: 3.89 g / DMAP / CH₂Cl₂ / 0.25 h / 0 °C

2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 99 percent / tetrahydrofuran / -78 - 20 °C

3.1: OsO₄; NaIO₄ / dioxane; H₂O / 24 h

4.1: 2.40 g / Jones reagent / acetone / 0.17 h / 0 °C

5.1: 91 percent / NaH₂PO₄; Na-Hg / methanol / 0.5 h / 20 °C

6.1: DIBAL-H / toluene; hexane / 1 h / -78 °C

7.1: 1.66 g / PPTS / 3 h / 20 °C

With dmap; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; jones reagent; sodium amalgam; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; acetone; toluene; 1.1: mesylation / 2.1: Metallation / 2.2: Cyclization / 3.1: Oxidation / 4.1: Oxidation / 5.1: Reduction / 6.1: Reduction / 7.1: Methylation;
DOI:10.1016/S0040-4020(00)00730-4