Benzoic acid (2S,3R)-5-[(1R,3S)-1,3-dimethyl-4-(2-trimethylsilanyl-ethoxycarbonylamino)-butyl]-5-methoxy-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R)-5-[(1R,3S)-1,3-dimethyl-4-(2-trimethylsilanyl-ethoxycarbonylamino)-butyl]-5-methoxy-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-tetrahydro-furan-3-yl ester
• CAS No.: 880344-77-4
• Molecular Formula: C₃₀H₄₇NO₈Si
• Molecular Weight: 577.791

Synonyms:Benzoic acid (2S,3R)-5-[(1R,3S)-1,3-dimethyl-4-(2-trimethylsilanyl-ethoxycarbonylamino)-butyl]-5-methoxy-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-tetrahydro-furan-3-yl ester

Chemical Property of Benzoic acid (2S,3R)-5-[(1R,3S)-1,3-dimethyl-4-(2-trimethylsilanyl-ethoxycarbonylamino)-butyl]-5-methoxy-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-tetrahydro-furan-3-yl ester

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Technology Process of Benzoic acid (2S,3R)-5-[(1R,3S)-1,3-dimethyl-4-(2-trimethylsilanyl-ethoxycarbonylamino)-butyl]-5-methoxy-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-tetrahydro-furan-3-yl ester

There total 2 articles about Benzoic acid (2S,3R)-5-[(1R,3S)-1,3-dimethyl-4-(2-trimethylsilanyl-ethoxycarbonylamino)-butyl]-5-methoxy-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-tetrahydro-furan-3-yl 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:

Benzoic acid (2S,3R)-5-((1R,3S)-4-azido-1,3-dimethyl-butyl)-5-methoxy-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-tetrahydro-furan-3-yl ester (343782-92-3) → Benzoic acid (2S,3R)-5-[(1R,3S)-1,3-dimethyl-4-(2-trimethylsilanyl-ethoxycarbonylamino)-butyl]-5-methoxy-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-tetrahydro-furan-3-yl ester (880344-77-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂; Pd/C catalyst / ethyl acetate / 7 h / 25 °C

2: 2.03 g / Et₃N / ethyl acetate / 15 h / 25 °C

With palladium on activated charcoal; hydrogen; triethylamine; In ethyl acetate;

DOI:10.1021/ja0547477

Reference yield:

2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate (80149-80-0) + Benzoic acid (2S,3R)-5-((1R,3S)-4-amino-1,3-dimethyl-butyl)-5-methoxy-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-tetrahydro-furan-3-yl ester → Benzoic acid (2S,3R)-5-[(1R,3S)-1,3-dimethyl-4-(2-trimethylsilanyl-ethoxycarbonylamino)-butyl]-5-methoxy-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-tetrahydro-furan-3-yl ester (880344-77-4)

Guidance literature:

With triethylamine; In ethyl acetate; at 25 ℃; for 12h;

DOI:10.1002/anie.200351825

Reference yield: 81.0%

Benzoic acid (2S,3R)-5-[(1R,3S)-1,3-dimethyl-4-(2-trimethylsilanyl-ethoxycarbonylamino)-butyl]-5-methoxy-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-tetrahydro-furan-3-yl ester (880344-77-4) → (2S,3R,5R,8S,10R)-3-Benzoyloxy-8,10-dimethyl-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid 2-trimethylsilanyl-ethyl ester (615285-01-3)

Guidance literature:

With neodymium(III) trifluoromethanesufonate; In acetonitrile; at 25 ℃; for 0.25h;

DOI:10.1021/ja0547477

upstream raw materials:

2-(Trimethylsilyl)ethyl 4-nitrophenyl carbonate

Benzoic acid (2S,3R)-5-((1R,3S)-4-azido-1,3-dimethyl-butyl)-5-methoxy-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-tetrahydro-furan-3-yl ester

Downstream raw materials:

(2S,3R,5R,8S,10R)-3-Benzoyloxy-8,10-dimethyl-2-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-1-oxa-6-aza-spiro[4.5]decane-6-carboxylic acid 2-trimethylsilanyl-ethyl ester

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