N-benzyloxyacetyl-N-(2-trimethylsilylethoxycarbonyl)-mycalamine

Base Information

• Chemical Name: N-benzyloxyacetyl-N-(2-trimethylsilylethoxycarbonyl)-mycalamine
• CAS No.: 1054630-14-6
• Molecular Formula: C₂₉H₄₃NO₁₁Si
• Molecular Weight: 609.746
• Mol file: 1054630-14-6.mol

Synonyms:N-benzyloxyacetyl-N-(2-trimethylsilylethoxycarbonyl)-mycalamine

Chemical Property of N-benzyloxyacetyl-N-(2-trimethylsilylethoxycarbonyl)-mycalamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyloxyacetyl-N-(2-trimethylsilylethoxycarbonyl)-mycalamine

There total 3 articles about N-benzyloxyacetyl-N-(2-trimethylsilylethoxycarbonyl)-mycalamine 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%

Benzyloxyacetyl chloride (19810-31-2) + [(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester (168072-64-8) → N-benzyloxyacetyl-N-(2-trimethylsilylethoxycarbonyl)-mycalamine (1054630-14-6)

Guidance literature:

[(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester; With dmap; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃;

Benzyloxyacetyl chloride; In tetrahydrofuran; at -78 - 0 ℃; for 1h; Further stages.;

DOI:10.1021/ol005629l

Reference yield:

2-(Trimethylsilyl)ethanol (2916-68-9) → N-benzyloxyacetyl-N-(2-trimethylsilylethoxycarbonyl)-mycalamine (1054630-14-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 83 percent / Ph₂PON₃; Et₃N; molecular sieves / tetrahydrofuran / 65 °C

2.1: LiHDMS; DMAP / tetrahydrofuran / -78 - 0 °C

2.2: 92 percent / tetrahydrofuran / 1 h / -78 - 0 °C

With dmap; molecular sieve; diphenylphosphoranyl azide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1.1: Curtius reaction / 2.1: deprotonation / 2.2: Substitution;

DOI:10.1021/ol005629l

Reference yield:

(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-4-carboxylic acid (168072-75-1) → N-benzyloxyacetyl-N-(2-trimethylsilylethoxycarbonyl)-mycalamine (1054630-14-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 83 percent / Ph₂PON₃; Et₃N; molecular sieves / tetrahydrofuran / 65 °C

2.1: LiHDMS; DMAP / tetrahydrofuran / -78 - 0 °C

2.2: 92 percent / tetrahydrofuran / 1 h / -78 - 0 °C

With dmap; molecular sieve; diphenylphosphoranyl azide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1.1: Curtius reaction / 2.1: deprotonation / 2.2: Substitution;

DOI:10.1021/ol005629l

upstream raw materials:

Benzyloxyacetyl chloride

[(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester

2-(Trimethylsilyl)ethanol

(4S,4aS,6R,8S,8aR)-8-Methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-4-carboxylic acid

Downstream raw materials:

mycalamide A

[benzyloxy-(4-hydroxy-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-acetyl]-[8-methoxy-7,7-dimethyl-6-(2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-carbamic acid 2-trimethylsilanyl-ethyl ester