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

Base Information

• Chemical Name: 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
• CAS No.: 441352-51-8
• Molecular Formula: C₄₃H₅₀O₈
• Molecular Weight: 694.865

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 48 articles about 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 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: 96.0%

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) → 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 (441352-51-8)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 3h;

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

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-((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 (441352-51-8)

Guidance literature:

Multi-step reaction with 13 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

13.1: 96 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °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; diisobutylaluminium 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-((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 (441352-51-8)

Guidance literature:

Multi-step reaction with 14 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

14.1: 96 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °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; diisobutylaluminium 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

upstream raw materials:

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

2-deoxy-D-ribose

benzyl bromide

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

Downstream raw materials:

(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

(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-4,8-bis-benzyloxy-9-benzyloxymethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-ol

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