(1S,3a⁽¹⁾R,5aS,6S,6aR,8S,9S,10aR,10bS)-8,9-dimethoxy-1-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-8,9-dimethyl-3a1,5a,6,6a,8,9,10a,10b-octahydro-1H-[1,4]dioxino[2',3':5,6]naphtho[1,8-cd]isoxazole

Base Information

• Chemical Name: (1S,3a⁽¹⁾R,5aS,6S,6aR,8S,9S,10aR,10bS)-8,9-dimethoxy-1-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-8,9-dimethyl-3a1,5a,6,6a,8,9,10a,10b-octahydro-1H-[1,4]dioxino[2',3':5,6]naphtho[1,8-cd]isoxazole
• CAS No.: 944455-64-5
• Molecular Formula: C₂₆H₃₅NO₈
• Molecular Weight: 489.566

Synonyms:(1S,3a⁽¹⁾R,5aS,6S,6aR,8S,9S,10aR,10bS)-8,9-dimethoxy-1-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-8,9-dimethyl-3a1,5a,6,6a,8,9,10a,10b-octahydro-1H-[1,4]dioxino[2',3':5,6]naphtho[1,8-cd]isoxazole

Chemical Property of (1S,3a⁽¹⁾R,5aS,6S,6aR,8S,9S,10aR,10bS)-8,9-dimethoxy-1-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-8,9-dimethyl-3a1,5a,6,6a,8,9,10a,10b-octahydro-1H-[1,4]dioxino[2',3':5,6]naphtho[1,8-cd]isoxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (1S,3a⁽¹⁾R,5aS,6S,6aR,8S,9S,10aR,10bS)-8,9-dimethoxy-1-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-8,9-dimethyl-3a1,5a,6,6a,8,9,10a,10b-octahydro-1H-[1,4]dioxino[2',3':5,6]naphtho[1,8-cd]isoxazole

There total 15 articles about (1S,3a⁽¹⁾R,5aS,6S,6aR,8S,9S,10aR,10bS)-8,9-dimethoxy-1-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-8,9-dimethyl-3a1,5a,6,6a,8,9,10a,10b-octahydro-1H-[1,4]dioxino[2',3':5,6]naphtho[1,8-cd]isoxazole 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: 92.0%

C26H37O8N (944455-62-3) → (1S,3a(1)R,5aS,6S,6aR,8S,9S,10aR,10bS)-8,9-dimethoxy-1-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-8,9-dimethyl-3a1,5a,6,6a,8,9,10a,10b-octahydro-1H-[1,4]dioxino[2',3':5,6]naphtho[1,8-cd]isoxazole (944455-64-5)

Guidance literature:

With pyridine; N-chloro-succinimide; In chloroform; at 40 - 60 ℃; for 1.16667h;

DOI:10.1016/j.tet.2007.02.126

Reference yield: 92.0%

(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 (1403352-61-3) → (1S,3a(1)R,5aS,6S,6aR,8S,9S,10aR,10bS)-8,9-dimethoxy-1-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-8,9-dimethyl-3a1,5a,6,6a,8,9,10a,10b-octahydro-1H-[1,4]dioxino[2',3':5,6]naphtho[1,8-cd]isoxazole (944455-64-5)

Guidance literature:

With pyridine; N-chloro-succinimide; In chloroform; at 40 - 60 ℃; for 1.16667h; Inert atmosphere;

DOI:10.1002/chem.201200257

Reference yield:

(2S,3S,4aR,5S,8aR)-2,3-dimethoxy-5-(methoxymethyl)-2,3-dimethyl-2,3,4a,5-tetrahydrobenzo[b][1,4]dioxin-6(8aH)-one (931095-12-4) → (1S,3a(1)R,5aS,6S,6aR,8S,9S,10aR,10bS)-8,9-dimethoxy-1-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-8,9-dimethyl-3a1,5a,6,6a,8,9,10a,10b-octahydro-1H-[1,4]dioxino[2',3':5,6]naphtho[1,8-cd]isoxazole (944455-64-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 100 percent / CeCl₃; NaBH₄ / methanol / 0.25 h / 0 °C

2.1: 93 percent / Ph₃P; DEAD / CH₂Cl₂; tetrahydrofuran / 24.5 h / 0 - 4 °C

3.1: 91 percent / TMSCl; triethylamine; LiHMDS / tetrahydrofuran; toluene / 2.5 h / -78 - 20 °C

4.1: toluene; methanol / 20 °C

5.1: 80 percent / DIBAH / CH₂Cl₂ / 3.5 h / -78 °C

6.1: 18-crown-6-ether; KHMDS / tetrahydrofuran / 0.25 h / -78 °C

6.2: 88 percent / tetrahydrofuran / 6 h / -90 - -80 °C

7.1: DIBAH / CH₂Cl₂ / 5 h / -78 °C

8.1: 99 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 20 °C

9.1: 61 percent / hydroxylamine hydrochloride; polymer-supported 2,6-di-tert-butyl-pyridine / tetrahydrofuran / 24 h / 40 °C

10.1: 92 percent / NCS; pyridine / CHCl₃ / 1.17 h / 40 - 60 °C

With pyridine; sodium tetrahydroborate; N-chloro-succinimide; chloro-trimethyl-silane; cerium(III) chloride; 18-crown-6 ether; hydroxylamine hydrochloride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; chloroform; toluene; 2.1: Mitsunobu reaction / 6.2: Still-Gennari olefination;

DOI:10.1016/j.tet.2007.02.126

upstream raw materials:

C₂₆H₃₇O₈N

(2S,3S,4aR,5S,8aR)-2,3-dimethoxy-5-(methoxymethyl)-2,3-dimethyl-2,3,4a,5-tetrahydrobenzo[b][1,4]dioxin-6(8aH)-one

C₂₅H₃₆O₉

C₂₄H₃₄O₈

Downstream raw materials:

(1R,2S,3S,3a1R,5aS,6S,6aR,8S,9S,10aR,10bS)-8,9-dimethoxy-1-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-8,9-dimethyl-2,3,3a1,5a,6,6a,8,9,10a,10b-decahydro-1H-[1,4]dioxino[2',3':5,6]naphtho[1,8-cd]isoxazole-2,3-diol

C₂₅H₃₃O₇N

(3aS,3b⁽¹⁾R,5aS,6S,6aR,8S,9S,10aR,10bS,11R,11aR)-8,9-dimethoxy-11-((4-methoxybenzyl)oxy)-6-(methoxymethyl)-2,2,8,9-tetramethyl-3b⁽¹⁾,5a,6,6a,8,9,10a,10b,11,11a-decahydro-3aH-[1,4]dioxino[2',3':5,6][1,3]dioxolo[4',5':2,3]naphtho[1,8-cd]isoxazole

(2S,3S,4aR,5R,6R,6aS,7aR,10aR,11R,11aS,11bR)-6-hydroxy-2,3-dimethoxy-11-((4-methoxybenzyl)oxy)-5-(methoxymethyl)-2,3,9,9-tetramethyldecahydro-[1,3]dioxolo[4',5':6,7]naphtho[1,2-b][1,4]dioxin-7(7aH)-one

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