Benzoic acid (1R,2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-1-((S)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-ethyl]-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester

Base Information

• Chemical Name: Benzoic acid (1R,2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-1-((S)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-ethyl]-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester
• CAS No.: 175612-28-9
• Molecular Formula: C₃₂H₅₄O₉SSi
• Molecular Weight: 642.927

Synonyms:Benzoic acid (1R,2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-1-((S)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-ethyl]-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester

Chemical Property of Benzoic acid (1R,2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-1-((S)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-ethyl]-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester

Chemical Property:

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Technology Process of Benzoic acid (1R,2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-1-((S)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-ethyl]-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester

There total 21 articles about Benzoic acid (1R,2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-1-((S)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-ethyl]-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl 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 (1R,2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-1-[(R)-1-((S)-2-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-ethyl]-hexyl ester → Benzoic acid (1R,2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-1-((S)-2,2-dioxo-2λ6-[1,3,2]dioxathiolan-4-yl)-ethyl]-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester (175612-28-9)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 0 ℃; for 1.5h; Yield given;

Reference yield:

(S)-1-(1-Ethylpropylidenamino)-2-methoxymethylpyrrolidin (59983-36-7) → Benzoic acid (1R,2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-1-((S)-2,2-dioxo-2λ6-[1,3,2]dioxathiolan-4-yl)-ethyl]-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester (175612-28-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) LDA / 1.) Et₂O, hexane, 0 deg C, 4 h, 2.) Et₂O, hexane, from -110 deg C to RT, 12 h

2: 97 percent / O₃ / CH₂Cl₂ / -78 °C

3: 1.) TiCl₄, Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.5 h, 2.) CH₂Cl₂, -78 deg C, 2.5 h

4: 89 percent / SmI₂ / tetrahydrofuran / 1 h / -10 °C

5: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 20 °C

6: 99 percent / H₂ / 10percent Pd/C / ethanol / 48 h / Ambient temperature

7: Et₃N, SOCl₂ / CH₂Cl₂ / 0.17 h / 0 °C

8: RuCl₃, NaIO₄ / CCl₄; acetonitrile; H₂O / 1.5 h / 0 °C

With 2,6-dimethylpyridine; ruthenium trichloride; sodium periodate; thionyl chloride; samarium diiodide; hydrogen; titanium tetrachloride; ozone; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; acetonitrile;

Reference yield:

L-rhamnose (73-34-7) → Benzoic acid (1R,2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(R)-1-((S)-2,2-dioxo-2λ6-[1,3,2]dioxathiolan-4-yl)-ethyl]-6-((2S,4R,6S)-4-methoxy-6-methyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-hexyl ester (175612-28-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 91 percent / 4-DMAP, Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: 81 percent / BF₃*Et₂O, TMSOTf / acetonitrile / 3 h / 0 °C

3: 100 percent / MeONa / methanol / 24 h / 25 °C

4: 1.) n-Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 4 h, 2.) DMF, 40 deg C, 16 h

5: 1.) imidazole, NaH

6: 60 percent / n-Bu₃SnH, AIBN / toluene / 1 h / 110 °C

7: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 20 min, 2.) CH₂Cl₂, MeOH, from -78 deg C to RT, 7 h

8: 83 percent / Ph₃P, I₂, imidazole / CH₂Cl₂ / 2 h / 40 °C

9: 1.) LDA / 1.) Et₂O, hexane, 0 deg C, 4 h, 2.) Et₂O, hexane, from -110 deg C to RT, 12 h

10: 97 percent / O₃ / CH₂Cl₂ / -78 °C

11: 1.) TiCl₄, Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.5 h, 2.) CH₂Cl₂, -78 deg C, 2.5 h

12: 89 percent / SmI₂ / tetrahydrofuran / 1 h / -10 °C

13: 86 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 20 °C

14: 99 percent / H₂ / 10percent Pd/C / ethanol / 48 h / Ambient temperature

15: Et₃N, SOCl₂ / CH₂Cl₂ / 0.17 h / 0 °C

16: RuCl₃, NaIO₄ / CCl₄; acetonitrile; H₂O / 1.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; thionyl chloride; samarium diiodide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; hydrogen; iodine; tri-n-butyl-tin hydride; sodium methylate; titanium tetrachloride; sodium hydride; di(n-butyl)tin oxide; ozone; triethylamine; triphenylphosphine; cesium fluoride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; water; toluene; acetonitrile;

upstream raw materials:

(S)-1-(1-Ethylpropylidenamino)-2-methoxymethylpyrrolidin

L-rhamnose

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

3-(2,3,4-tri-O-acetyl-L-rhamnosyl)-1-propene

Downstream raw materials:

C₆₀H₁₀₄O₁₂Si₂

C₅₉H₁₀₂O₁₂Si₂

C₅₉H₁₀₀O₁₁Si₂

C₆₂H₁₁₂O₁₁Si₃

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