Benzoic acid (2R,3R,4aR,6R,7aS,9R,10S,11aR,12aS)-3-((R)-2-cyano-1-triisopropylsilanyloxy-ethyl)-6-hydroxymethyl-10-methoxy-9-methoxymethyl-3-methyl-dodecahydro-4,8,12-trioxa-dibenzo[a,d]cycloocten-2-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4aR,6R,7aS,9R,10S,11aR,12aS)-3-((R)-2-cyano-1-triisopropylsilanyloxy-ethyl)-6-hydroxymethyl-10-methoxy-9-methoxymethyl-3-methyl-dodecahydro-4,8,12-trioxa-dibenzo[a,d]cycloocten-2-yl ester
• CAS No.: 685885-65-8
• Molecular Formula: C₃₇H₅₉NO₉Si
• Molecular Weight: 689.962

Synonyms:Benzoic acid (2R,3R,4aR,6R,7aS,9R,10S,11aR,12aS)-3-((R)-2-cyano-1-triisopropylsilanyloxy-ethyl)-6-hydroxymethyl-10-methoxy-9-methoxymethyl-3-methyl-dodecahydro-4,8,12-trioxa-dibenzo[a,d]cycloocten-2-yl ester

Chemical Property of Benzoic acid (2R,3R,4aR,6R,7aS,9R,10S,11aR,12aS)-3-((R)-2-cyano-1-triisopropylsilanyloxy-ethyl)-6-hydroxymethyl-10-methoxy-9-methoxymethyl-3-methyl-dodecahydro-4,8,12-trioxa-dibenzo[a,d]cycloocten-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3R,4aR,6R,7aS,9R,10S,11aR,12aS)-3-((R)-2-cyano-1-triisopropylsilanyloxy-ethyl)-6-hydroxymethyl-10-methoxy-9-methoxymethyl-3-methyl-dodecahydro-4,8,12-trioxa-dibenzo[a,d]cycloocten-2-yl ester

There total 19 articles about Benzoic acid (2R,3R,4aR,6R,7aS,9R,10S,11aR,12aS)-3-((R)-2-cyano-1-triisopropylsilanyloxy-ethyl)-6-hydroxymethyl-10-methoxy-9-methoxymethyl-3-methyl-dodecahydro-4,8,12-trioxa-dibenzo[a,d]cycloocten-2-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: 93.0%

Benzoic acid (2R,3R,4aR,7aS,9R,10S,11aR,12aS)-3-((R)-2-cyano-1-triisopropylsilanyloxy-ethyl)-6-formyl-10-methoxy-9-methoxymethyl-3-methyl-dodecahydro-4,8,12-trioxa-dibenzo[a,d]cycloocten-2-yl ester → Benzoic acid (2R,3R,4aR,6R,7aS,9R,10S,11aR,12aS)-3-((R)-2-cyano-1-triisopropylsilanyloxy-ethyl)-6-hydroxymethyl-10-methoxy-9-methoxymethyl-3-methyl-dodecahydro-4,8,12-trioxa-dibenzo[a,d]cycloocten-2-yl ester (685885-65-8)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In acetonitrile; at -10 - 0 ℃; for 5h;

DOI:10.1055/s-2004-817769

Reference yield:

[(4R,5S)-2,2,5-Trimethyl-5-((R)-3-oxo-1-triethylsilanyloxy-propyl)-[1,3]dioxolan-4-yl]-acetonitrile (524734-72-3) → Benzoic acid (2R,3R,4aR,6R,7aS,9R,10S,11aR,12aS)-3-((R)-2-cyano-1-triisopropylsilanyloxy-ethyl)-6-hydroxymethyl-10-methoxy-9-methoxymethyl-3-methyl-dodecahydro-4,8,12-trioxa-dibenzo[a,d]cycloocten-2-yl ester (685885-65-8)

Guidance literature:

Multi-step reaction with 14 steps

1.1: n-BuLi / tetrahydrofuran

2.1: TBAF / tetrahydrofuran

3.1: 99 percent / CuI; n-PrNH₂ / Pd(PPh₃)4 / toluene

4.1: 100 percent / pyridine; DMAP / CH₂Cl₂

5.1: HF*pyridine / acetonitrile

6.1: BF₃*OEt₂ / CH₂Cl₂

7.1: 93 percent / pyridine / dimethylformamide / 48 h / 0 - 20 °C

8.1: 83 percent / n-BuLi / tetrahydrofuran / 1.25 h / -78 °C

9.1: CSA / methanol / 6 h / 20 °C

10.1: toluene / 85 °C

11.1: n-Bu₃SnH; AIBN / toluene / 0.08 h / 95 °C

12.1: IBX / dimethylsulfoxide / 20 h / 20 °C

12.2: 99 percent / DBU / tetrahydrofuran / 1 h / 0 - 20 °C

13.1: 93 percent / NaBH(OAc)3; AcOH / acetonitrile / 5 h / -10 - 0 °C

With pyridine; propylamine; dmap; copper(l) iodide; n-butyllithium; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium tris(acetoxy)borohydride; pyridine hydrogenfluoride; acetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1055/s-2004-817769

Reference yield:

1-((2S,3R,5S,6R)-3-Hydroxy-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-propan-2-one → Benzoic acid (2R,3R,4aR,6R,7aS,9R,10S,11aR,12aS)-3-((R)-2-cyano-1-triisopropylsilanyloxy-ethyl)-6-hydroxymethyl-10-methoxy-9-methoxymethyl-3-methyl-dodecahydro-4,8,12-trioxa-dibenzo[a,d]cycloocten-2-yl ester (685885-65-8)

Guidance literature:

Multi-step reaction with 14 steps

1.1: PPTS / CH₂Cl₂

2.1: LDA / tetrahydrofuran / -78 °C

2.2: tetrahydrofuran / 20 °C

2.3: CSA / methanol

3.1: 99 percent / CuI; n-PrNH₂ / Pd(PPh₃)4 / toluene

4.1: 100 percent / pyridine; DMAP / CH₂Cl₂

5.1: HF*pyridine / acetonitrile

6.1: BF₃*OEt₂ / CH₂Cl₂

7.1: 93 percent / pyridine / dimethylformamide / 48 h / 0 - 20 °C

8.1: 83 percent / n-BuLi / tetrahydrofuran / 1.25 h / -78 °C

9.1: CSA / methanol / 6 h / 20 °C

10.1: toluene / 85 °C

11.1: n-Bu₃SnH; AIBN / toluene / 0.08 h / 95 °C

12.1: IBX / dimethylsulfoxide / 20 h / 20 °C

12.2: 99 percent / DBU / tetrahydrofuran / 1 h / 0 - 20 °C

13.1: 93 percent / NaBH(OAc)3; AcOH / acetonitrile / 5 h / -10 - 0 °C

With pyridine; propylamine; dmap; copper(l) iodide; n-butyllithium; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium tris(acetoxy)borohydride; pyridine hydrogenfluoride; acetic acid; lithium diisopropyl amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1055/s-2004-817769

upstream raw materials:

[(4R,5S)-2,2,5-Trimethyl-5-((R)-3-oxo-1-triethylsilanyloxy-propyl)-[1,3]dioxolan-4-yl]-acetonitrile

(3R,5S,6R)-3-Benzyloxy-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-one

(2S,3R,5S,6R)-3-Benzyloxy-2,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran

[(4R,5R)-5-((R)-1,3-Dihydroxy-pent-4-ynyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-acetonitrile

Downstream raw materials:

Benzoic acid (2R,3R,4aR,6R,7aS,9R,10S,11aR,12aS)-3-((R)-2-cyano-1-triisopropylsilanyloxy-ethyl)-6-(imidazole-1-carbothioyloxymethyl)-10-methoxy-9-methoxymethyl-3-methyl-dodecahydro-4,8,12-trioxa-dibenzo[a,d]cycloocten-2-yl ester

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