(S,2Z)-4-((2S,3S,4aR,5S,8S,8aR)-2,3-dimethoxy-8-(methoxymethyl)-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-yl)-4-((4-methoxybenzyl)oxy)but-2-enal oxime

Base Information

Chemical Name:(S,2Z)-4-((2S,3S,4aR,5S,8S,8aR)-2,3-dimethoxy-8-(methoxymethyl)-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-yl)-4-((4-methoxybenzyl)oxy)but-2-enal oxime
CAS No.:1403352-61-3
Molecular Formula:C₂₆H₃₇NO₈
Molecular Weight:491.582
Hs Code.:

(S,2Z)-4-((2S,3S,4aR,5S,8S,8aR)-2,3-dimethoxy-8-(methoxymethyl)-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-yl)-4-((4-methoxybenzyl)oxy)but-2-enal oxime

Synonyms:(S,2Z)-4-((2S,3S,4aR,5S,8S,8aR)-2,3-dimethoxy-8-(methoxymethyl)-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-yl)-4-((4-methoxybenzyl)oxy)but-2-enal oxime

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Chemical Property of (S,2Z)-4-((2S,3S,4aR,5S,8S,8aR)-2,3-dimethoxy-8-(methoxymethyl)-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-yl)-4-((4-methoxybenzyl)oxy)but-2-enal oxime

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Technology Process of (S,2Z)-4-((2S,3S,4aR,5S,8S,8aR)-2,3-dimethoxy-8-(methoxymethyl)-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-yl)-4-((4-methoxybenzyl)oxy)but-2-enal oxime

There total 7 articles about (S,2Z)-4-((2S,3S,4aR,5S,8S,8aR)-2,3-dimethoxy-8-(methoxymethyl)-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-yl)-4-((4-methoxybenzyl)oxy)but-2-enal oxime 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: 61.0%

: (S,Z)-4-((2S,3S,4aR,5S,8S,8aR)-2,3-dimethoxy-8-(methoxymethyl)-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-yl)-4-((4-methoxybenzyl)oxy)but-2-enal

: 1403352-61-3
(S,2Z)-4-((2S,3S,4aR,5S,8S,8aR)-2,3-dimethoxy-8-(methoxymethyl)-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-yl)-4-((4-methoxybenzyl)oxy)but-2-enal oxime

Guidance literature:: With hydroxylamine hydrochloride; In tetrahydrofuran; at 40 ℃; for 24h; Inert atmosphere;
DOI:10.1002/chem.201200257

Reference yield:

: 944455-58-7
(2S,3S,4aR,5R,6R,8aR)-2,3-dimethoxy-5-(methoxymethyl)-2,3-dimethyl-2,3,4a,5,6,8a-hexahydrobenzo[b][1,4]dioxin-6-yl 2-((4-methoxybenzyl)oxy)acetate

: 1403352-61-3
(S,2Z)-4-((2S,3S,4aR,5S,8S,8aR)-2,3-dimethoxy-8-(methoxymethyl)-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-yl)-4-((4-methoxybenzyl)oxy)but-2-enal oxime

Guidance literature:: Multi-step reaction with 7 steps

1.1: chloro-trimethyl-silane; triethylamine / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

1.2: 2.5 h / -78 - 20 °C / Inert atmosphere

2.1: methanol; toluene / 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane / 3.5 h / -78 °C / Inert atmosphere

4.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere

4.2: 6 h / -90 - -80 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 5 h / -78 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere

7.1: hydroxylamine hydrochloride / tetrahydrofuran / 24 h / 40 °C / Inert atmosphere

With chloro-trimethyl-silane; 18-crown-6 ether; hydroxylamine hydrochloride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Burke-Kallmerten-Claisen rearrangement / 1.2: Burke-Kallmerten-Claisen rearrangement;
DOI:10.1002/chem.201200257

Reference yield:

: (R)-2-((2S,3S,4aR,5R,8S,8aR)-2,3-dimethoxy-8-(methoxymethyl)-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-yl)-2-((4-methoxybenzyl)oxy)acetaldehyde

: 1403352-61-3
(S,2Z)-4-((2S,3S,4aR,5S,8S,8aR)-2,3-dimethoxy-8-(methoxymethyl)-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxin-5-yl)-4-((4-methoxybenzyl)oxy)but-2-enal oxime

Guidance literature:: Multi-step reaction with 4 steps

1.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere

1.2: 6 h / -90 - -80 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane / 5 h / -78 °C / Inert atmosphere

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere

4.1: hydroxylamine hydrochloride / tetrahydrofuran / 24 h / 40 °C / Inert atmosphere

With 18-crown-6 ether; hydroxylamine hydrochloride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.201200257