(4R,6S)-2,2-dimethyl-4-[(1E)-2-phenylethenyl]-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxane

Base Information

Chemical Name:(4R,6S)-2,2-dimethyl-4-[(1E)-2-phenylethenyl]-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxane
CAS No.:1428899-26-6
Molecular Formula:C₂₉H₃₂O₃
Molecular Weight:428.571
Hs Code.:

Synonyms:(4R,6S)-2,2-dimethyl-4-[(1E)-2-phenylethenyl]-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxane

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Chemical Property of (4R,6S)-2,2-dimethyl-4-[(1E)-2-phenylethenyl]-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxane

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Technology Process of (4R,6S)-2,2-dimethyl-4-[(1E)-2-phenylethenyl]-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxane

There total 14 articles about (4R,6S)-2,2-dimethyl-4-[(1E)-2-phenylethenyl]-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxane 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: 75.0%

: 1428899-28-8
(4R,6S)-2,2-dimethyl-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxan-4-carboxaldehyde

: 1449-46-3
benzyltriphenylphosphonium bromide

: 1428899-26-6
(4R,6S)-2,2-dimethyl-4-[(1E)-2-phenylethenyl]-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxane

: (4R,6S)-2,2-dimethyl-4-[(1Z)-2-phenylethenyl]-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxane

Guidance literature:: benzyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; Inert atmosphere;

(4R,6S)-2,2-dimethyl-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxan-4-carboxaldehyde; In tetrahydrofuran; hexane; at 20 ℃; for 4h;
DOI:10.1002/hlca.201200165

Reference yield:

: 123-08-0,65581-83-1
4-hydroxy-benzaldehyde

: 1428899-26-6
(4R,6S)-2,2-dimethyl-4-[(1E)-2-phenylethenyl]-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxane

: (4R,6S)-2,2-dimethyl-4-[(1Z)-2-phenylethenyl]-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxane

Guidance literature:: Multi-step reaction with 13 steps

1.1: sodium hydride / tetrahydrofuran / 4 h / 0 - 20 °C

2.1: dichloromethane / 8 h / 20 °C

3.1: lithium borohydride / water; diethyl ether / 24 h / 0 - 20 °C

4.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1.5 h / -78 °C

4.2: 0 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

5.2: 3 h / -78 °C

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Reflux

7.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

7.2: 5 h / -20 °C

8.1: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

8.2: 6 h / -20 °C

9.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2 h / 0 - 20 °C / Inert atmosphere

10.1: toluene-4-sulfonic acid / dichloromethane / 0.5 h / 20 °C

11.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 20 °C

12.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1.5 h / -78 °C

12.2: 0 °C

13.1: n-butyllithium / tetrahydrofuran; hexane / 20 °C / Inert atmosphere

13.2: 4 h / 20 °C

With titanium(IV) isopropylate; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; oxalyl dichloride; L-(+)-diisopropyl tartrate; sodium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; dimethyl sulfoxide; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; 2.1: |Wittig Olefination / 4.1: |Swern Oxidation / 4.2: |Swern Oxidation / 7.1: |Sharpless Asymmetric Epoxidation / 7.2: |Sharpless Asymmetric Epoxidation / 8.1: |Sharpless Asymmetric Epoxidation / 8.2: |Sharpless Asymmetric Epoxidation / 12.1: |Swern Oxidation / 12.2: |Swern Oxidation / 13.2: |Wittig Olefination;
DOI:10.1002/hlca.201200165

Reference yield:

: 1428899-25-5
(4R,6S)-2,2-dimethyl-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxan-4-methanol

: 1428899-26-6
(4R,6S)-2,2-dimethyl-4-[(1E)-2-phenylethenyl]-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxane

: (4R,6S)-2,2-dimethyl-4-[(1Z)-2-phenylethenyl]-6-{2-[4-(phenylmethoxy)phenyl]ethyl}-1,3-dioxane

Guidance literature:: Multi-step reaction with 2 steps

1.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1.5 h / -78 °C

1.2: 0 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 20 °C / Inert atmosphere

2.2: 4 h / 20 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; hexane; dichloromethane; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation / 2.2: |Wittig Olefination;
DOI:10.1002/hlca.201200165