[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

Base Information

• Chemical Name: [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
• CAS No.: 1054625-32-9
• Molecular Formula: C₃₇H₅₇NO₁₄Si
• Molecular Weight: 767.943
• Mol file: 1054625-32-9.mol

Synonyms:[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

Chemical Property of [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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [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

There total 7 articles about [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 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: 53.0%

[2-benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-3-oxo-octanoyl]-[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 → [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 + [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 (1054625-32-9)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; at 23 ℃; for 8h;

DOI:10.1021/ol005629l

Reference yield: 31.0%

[2-benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-methyl-octanoyl]-[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 → [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 + [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 (1054625-32-9)

Guidance literature:

[2-benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-methyl-octanoyl]-[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; With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane; at -78 - 0 ℃; for 5h;

With camphor-10-sulfonic acid; In methanol; at 23 ℃; for 8h; Further stages.;

DOI:10.1021/ol005629l

Reference yield:

N-benzyloxyacetyl-N-(2-trimethylsilylethoxycarbonyl)-mycalamine (1054630-14-6) → [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 (1054625-32-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TiCl₄; diisopropylethylamine / CH₂Cl₂ / 0.83 h / -78 °C

1.2: CH₂Cl₂ / 2.5 h / -78 °C

2.1: TFAA; DMSO; triethylamine / CH₂Cl₂ / 5 h / -78 - 0 °C

2.2: 27 percent / CSA / methanol / 8 h / 23 °C

With titanium tetrachloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In dichloromethane; 1.1: Rearrangement / 1.2: Addition / 2.1: Oxidation / 2.2: Cyclization;

DOI:10.1021/ol005629l

upstream raw materials:

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

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

[(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