Benzoic acid (R)-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethyl ester

Base Information

• Chemical Name: Benzoic acid (R)-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethyl ester
• CAS No.: 855282-15-4
• Molecular Formula: C₂₄H₃₈O₅Si
• Molecular Weight: 434.648
• Mol file: 855282-15-4.mol

Synonyms:Benzoic acid (R)-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethyl ester

Chemical Property of Benzoic acid (R)-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (R)-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethyl ester

There total 3 articles about Benzoic acid (R)-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-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: 94.0%

(R)-1-((2R,5R,6R)-2-Methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethanol (855282-47-2) + benzoyl chloride (98-88-4) → Benzoic acid (R)-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethyl ester (855282-15-4)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/ja050728l

Reference yield:

(R)-1-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)ethane-1,2-diol (855282-45-0) → Benzoic acid (R)-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethyl ester (855282-15-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / DIPEA / tetrahydrofuran

2: 94 percent / DMAP; DIPEA / tetrahydrofuran

With dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/ja050728l

Reference yield:

(5R,6R)-2-Methoxy-5,6-dimethyl-4-methylene-2-((R)-2-phenyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran → Benzoic acid (R)-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethyl ester (855282-15-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / Na; liquid ammonia; EtOH / tetrahydrofuran / 0.5 h / -78 °C

2: 93 percent / DIPEA / tetrahydrofuran

3: 94 percent / DMAP; DIPEA / tetrahydrofuran

With dmap; ethanol; ammonia; sodium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/ja050728l

upstream raw materials:

(R)-1-((2R,5R,6R)-2-Methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethanol

benzoyl chloride

(R)-1-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)ethane-1,2-diol

Downstream raw materials:

(S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid

Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

mycalamide A

(S)-2-methoxy-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-oxoethyl benzoate