tert-butyl[(2R,3S,5R)-3-((Z)-2-iodovinyl)-5-methoxytetrahydrofuran-2-ylmethoxy]diphenylsilane

Base Information

• Chemical Name: tert-butyl[(2R,3S,5R)-3-((Z)-2-iodovinyl)-5-methoxytetrahydrofuran-2-ylmethoxy]diphenylsilane
• CAS No.: 1403352-48-6
• Molecular Formula: C₂₄H₃₁IO₃Si
• Molecular Weight: 522.498
• Mol file: 1403352-48-6.mol

Synonyms:tert-butyl[(2R,3S,5R)-3-((Z)-2-iodovinyl)-5-methoxytetrahydrofuran-2-ylmethoxy]diphenylsilane

Chemical Property of tert-butyl[(2R,3S,5R)-3-((Z)-2-iodovinyl)-5-methoxytetrahydrofuran-2-ylmethoxy]diphenylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl[(2R,3S,5R)-3-((Z)-2-iodovinyl)-5-methoxytetrahydrofuran-2-ylmethoxy]diphenylsilane

There total 9 articles about tert-butyl[(2R,3S,5R)-3-((Z)-2-iodovinyl)-5-methoxytetrahydrofuran-2-ylmethoxy]diphenylsilane 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: 83.0%

(2R,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde + (iodomethyl)triphenylphosphonium iodide (3020-28-8) → tert-butyl[(2R,3S,5R)-3-((Z)-2-iodovinyl)-5-methoxytetrahydrofuran-2-ylmethoxy]diphenylsilane (1403352-48-6)

Guidance literature:

(iodomethyl)triphenylphosphonium iodide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 0.0166667h; Inert atmosphere;

(2R,3R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-tetrahydro-furan-3-carbaldehyde; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/chem.201200257

Reference yield:

L-gulono-1,4-lactone (1128-23-0) → tert-butyl[(2R,3S,5R)-3-((Z)-2-iodovinyl)-5-methoxytetrahydrofuran-2-ylmethoxy]diphenylsilane (1403352-48-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: sulfuric acid / N,N-dimethyl-formamide / 8 h / 20 °C / pH 3 / Inert atmosphere; Cooling with ice

2.1: sodium periodate; sodium hydroxide / water / 1 h / pH 5.5 / Inert atmosphere; Cooling with ice

2.2: 10 h / 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / benzene / Inert atmosphere

3.2: 24 h / Inert atmosphere

4.1: sodium periodate / methanol; water / 0 °C / Inert atmosphere

5.1: calcium carbonate / toluene / Inert atmosphere; Reflux

6.1: 1H-imidazole / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere

7.1: copper(l) chloride; lithium chloride / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

7.2: 0.67 h / Inert atmosphere; Cooling

8.1: diisobutylaluminium hydride / diethyl ether; toluene / 1 h / -78 °C / Inert atmosphere

9.1: silver(l) oxide / dichloromethane / 48 h / Inert atmosphere; Reflux

10.1: ozone / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

10.2: 0 °C / Inert atmosphere

11.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.02 h / 20 °C / Inert atmosphere

11.2: 0.5 h / -78 °C / Inert atmosphere

With 1H-imidazole; sodium periodate; sulfuric acid; sodium hexamethyldisilazane; diisobutylaluminium hydride; ozone; N-ethyl-N,N-diisopropylamine; calcium carbonate; copper(l) chloride; lithium chloride; sodium hydroxide; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 11.1: Wittig-Stork-Zhao olefination / 11.2: Wittig-Stork-Zhao olefination;

DOI:10.1002/chem.201200257

Reference yield:

tert-butyl (((2R,3S,5R)-5-methoxy-3-vinyl-tetrahydrofuran-2-yl)methoxy)diphenylsilane (909395-03-5) → tert-butyl[(2R,3S,5R)-3-((Z)-2-iodovinyl)-5-methoxytetrahydrofuran-2-ylmethoxy]diphenylsilane (1403352-48-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ozone / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.02 h / 20 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

With sodium hexamethyldisilazane; ozone; In tetrahydrofuran; dichloromethane; 2.1: Wittig-Stork-Zhao olefination / 2.2: Wittig-Stork-Zhao olefination;

DOI:10.1002/chem.201200257

upstream raw materials:

(iodomethyl)triphenylphosphonium iodide

tert-butyl (((2R,3S,5R)-5-methoxy-3-vinyl-tetrahydrofuran-2-yl)methoxy)diphenylsilane

ethyl (R,Z)-3-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)acrylate

ethyl (E)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate