2,2-Dimethyl-propionic acid 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethyl ester
• CAS No.: 441352-37-0
• Molecular Formula: C₄₈H₅₈O₉
• Molecular Weight: 778.983
• Mol file: 441352-37-0.mol

Synonyms:2,2-Dimethyl-propionic acid 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethyl ester

Chemical Property of 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethyl ester

There total 47 articles about 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-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:

isopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (69247-19-4,113019-32-2,23339-23-3) → 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethyl ester (441352-37-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: H₂ / 10 percent Pd/C / ethyl acetate; ethanol / 20 °C

2.1: NaOMe / methanol / 0.5 h / 20 °C

3.1: tetra-n-butylammonium iodide; NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

3.2: 5.89 g / tetrahydrofuran; dimethylformamide / 0 - 20 °C

4.1: 78 percent / aq. acetic acid; aq. HCl / 48 h / 60 °C

5.1: 78 percent / N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / acetonitrile / 4.5 h / 20 °C

6.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

6.2: tetrahydrofuran / 1.5 h / 0 °C

7.1: 9-BBN / tetrahydrofuran / 2 h / Heating

7.2: aq. Cs₂CO₃ / tetrahydrofuran / 0.25 h / 20 °C

7.3: 91 percent / Pd₂(dba)3*CHCl₃; Ph₃As / tetrahydrofuran; dimethylformamide / 14 h / 20 °C

8.1: thexylborane / tetrahydrofuran / 2 h / 0 °C

8.2: 92 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 20 - 45 °C

9.1: 99 percent / 4 Angstroem molecular sieves; N-methylmorpholine-N-oxide; tetra-N-propylammonium perruthenete / CH₂Cl₂ / 1 h / 20 °C

10.1: Me₃AL / CH₂Cl₂; hexane / 6 h / -78 °C

10.2: p-TsOH*H₂O / CH₂Cl₂

11.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

12.1: 123.1 mg / Et₃SiH; BF₃*OEt₂ / acetonitrile / 2 h / 0 °C

With hydrogenchloride; triethylsilane; dmap; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 4 A molecular sieve; thexylborane; boron trifluoride diethyl etherate; hydrogen; trimethylaluminum; sodium methylate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(02)00045-5

Reference yield:

D-glucal triacetate (2873-29-2) → 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethyl ester (441352-37-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: BF₃*OEt₂ / CH₂Cl₂ / 0 - 20 °C

2.1: H₂ / 10 percent Pd/C / ethyl acetate; ethanol / 20 °C

3.1: NaOMe / methanol / 0.5 h / 20 °C

4.1: tetra-n-butylammonium iodide; NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

4.2: 5.89 g / tetrahydrofuran; dimethylformamide / 0 - 20 °C

5.1: 78 percent / aq. acetic acid; aq. HCl / 48 h / 60 °C

6.1: 78 percent / N-methylmorpholine N-oxide; tetra-n-propylammonium perruthenate; 4 Angstroem molecular sieves / acetonitrile / 4.5 h / 20 °C

7.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

7.2: tetrahydrofuran / 1.5 h / 0 °C

8.1: 9-BBN / tetrahydrofuran / 2 h / Heating

8.2: aq. Cs₂CO₃ / tetrahydrofuran / 0.25 h / 20 °C

8.3: 91 percent / Pd₂(dba)3*CHCl₃; Ph₃As / tetrahydrofuran; dimethylformamide / 14 h / 20 °C

9.1: thexylborane / tetrahydrofuran / 2 h / 0 °C

9.2: 92 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 20 - 45 °C

10.1: 99 percent / 4 Angstroem molecular sieves; N-methylmorpholine-N-oxide; tetra-N-propylammonium perruthenete / CH₂Cl₂ / 1 h / 20 °C

11.1: Me₃AL / CH₂Cl₂; hexane / 6 h / -78 °C

11.2: p-TsOH*H₂O / CH₂Cl₂

12.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

13.1: 123.1 mg / Et₃SiH; BF₃*OEt₂ / acetonitrile / 2 h / 0 °C

With hydrogenchloride; triethylsilane; dmap; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 4 A molecular sieve; thexylborane; boron trifluoride diethyl etherate; hydrogen; trimethylaluminum; sodium methylate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(02)00045-5

Reference yield:

2,2-Dimethyl-propionic acid 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-tris-benzyloxy-9-benzyloxymethyl-5a-methoxy-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethyl ester → 2,2-Dimethyl-propionic acid 2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethyl ester (441352-37-0)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(02)00045-5

upstream raw materials:

2-deoxy-D-ribose

benzyl bromide

isopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester

Downstream raw materials:

(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-2-Allyl-4,8-bis-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-ol

(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-2-Allyl-3-allyloxy-4,8-bis-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-2-Allyl-3,4,8-tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

2-((2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4,8-Tris-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl)-ethanol