(2S,3S,4aR,8R,8aS)-methyl 8-(3-formyl-2-iodo-6-methoxyphenoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate

Base Information

• Chemical Name: (2S,3S,4aR,8R,8aS)-methyl 8-(3-formyl-2-iodo-6-methoxyphenoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate
• CAS No.: 1309662-63-2
• Molecular Formula: C₂₂H₂₇IO₉
• Molecular Weight: 562.355
• Mol file: 1309662-63-2.mol

Synonyms:(2S,3S,4aR,8R,8aS)-methyl 8-(3-formyl-2-iodo-6-methoxyphenoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate

Chemical Property of (2S,3S,4aR,8R,8aS)-methyl 8-(3-formyl-2-iodo-6-methoxyphenoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4aR,8R,8aS)-methyl 8-(3-formyl-2-iodo-6-methoxyphenoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate

There total 8 articles about (2S,3S,4aR,8R,8aS)-methyl 8-(3-formyl-2-iodo-6-methoxyphenoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate 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: 84.0%

(2S,3S,4aR,8S,8aS)-methyl 8-bromo-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate (1309662-66-5) + 2-iodoisovanillin (138490-94-5) → (2S,3S,4aR,8R,8aS)-methyl 8-(3-formyl-2-iodo-6-methoxyphenoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate (1309662-63-2)

Guidance literature:

With potassium carbonate; silver(l) oxide; In N,N-dimethyl-formamide; at 60 ℃; for 5h; Inert atmosphere; Sealed tube;

DOI:10.1016/j.tet.2011.03.063

Reference yield:

(2S,3S,4aR,8S,8aS)-methyl 8-bromo-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate (1309662-66-5) + 2-iodoisovanillin (138490-94-5) → (2S,3S,4aR,8S,8aS)-methyl 8-(3-formyl-2-iodo-6-methoxyphenoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate + (2S,3S,4aR,8R,8aS)-methyl 8-(3-formyl-2-iodo-6-methoxyphenoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate (1309662-63-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 18h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.tet.2011.03.063

Reference yield:

(2S,3S,4aR,8R,8aS)-methyl 2,3-dimethoxy-2,3-dimethyl-8-(methylsulfonyloxy)-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate (1309662-62-1) → (2S,3S,4aR,8R,8aS)-methyl 8-(3-formyl-2-iodo-6-methoxyphenoxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate (1309662-63-2)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium bromide / tetrahydrofuran / 20 °C / Inert atmosphere

2: potassium carbonate; silver(l) oxide / N,N-dimethyl-formamide / 5 h / 60 °C / Inert atmosphere; Sealed tube

With potassium carbonate; lithium bromide; silver(l) oxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2011.03.063

upstream raw materials:

(2S,3S,4aR,8S,8aS)-methyl 8-bromo-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate

2-iodoisovanillin

(2S,3S,4aR,8R,8aS)-methyl 2,3-dimethoxy-2,3-dimethyl-8-(methylsulfonyloxy)-2,3,4a,5,8,8a-hexahydrobenzo[b][1,4]dioxine-6-carboxylate

shikimic acid