(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

Base Information

• Chemical Name: (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
• CAS No.: 441352-41-6
• Molecular Formula: C₃₇H₄₄O₇
• Molecular Weight: 600.752
• Mol file: 441352-41-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 58 articles about (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 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%

(3aS,4aR,5aS,7R,8S,10aR,11aR,12S,12aS)-8,12-Bis-benzyloxy-7-benzyloxymethyl-2-iodomethyl-tetradecahydro-1,4,6,11-tetraoxa-cyclohepta[b]cyclopenta[g]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 (441352-41-6)

Guidance literature:

With acetic acid; zinc; In methanol; diethyl ether; at 20 ℃;

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

Reference yield:

2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)ethanol (81972-20-5) → (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 (441352-41-6)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 100 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

2.1: hydrogen / Pd(OH)2/C / ethyl acetate; methanol / 20 °C

3.1: CSA / dimethylformamide; CH₂Cl₂ / 20 °C

4.1: NaHMDS; Bu₄NI / dimethylformamide / 0 °C

5.1: CSA; MeOH / CH₂Cl₂ / 20 °C

6.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

7.1: DIBAL-H / CH₂Cl₂ / -78 °C

8.1: i-Pr₂NEt; Bu₄NI / CH₂Cl₂ / 0 °C

9.1: CSA; MeOH / CH₂Cl₂ / 0 °C

10.1: 100 percent / I₂; imidazole; PPh₃ / benzene / 20 °C

11.1: 96 percent / t-BuOK / tetrahydrofuran / 0 °C

12.1: tetrahydrofuran / 2 h / 60 °C

13.1: NaHCO₃ / Pd(PPh₃)4 / H₂O; tetrahydrofuran; dimethylformamide / 20 h / 50 °C

13.2: 243.1 mg / NaOH; aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

14.1: 2,3-dimethyl-2-butene; BH₃*THF / tetrahydrofuran / -20 - 0 °C

14.2: 73 percent / NaOH; aq. H₂O₂ / tetrahydrofuran / 2 h

15.1: (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

16.1: 55.4 mg / p-TsOH*H₂O / CH₂Cl₂ / 22 h / 20 - 55 °C

17.1: SO₃*pyridine complex; triethylamine; DMSO / CH₂Cl₂ / 0 - 20 °C

18.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

18.2: 39.3 mg / tetrahydrofuran; CH₂Cl₂ / 1 h / 0 °C

19.1: 86 percent / BF₃*Et₂O; Et₃SiH / acetonitrile; CH₂Cl₂ / 0 - 20 °C

20.1: iodine / CH₂Cl₂ / 0 - 20 °C

20.2: 17.7 mg / zinc; acetic acid / diethyl ether; methanol / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; methanol; triethylsilane; dmap; 2,3-Dimethyl-2-butene; borane-THF; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; iodine; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; benzene; 13.1: Suzuki cross-coupling / 15.1: Swern oxidation / 18.2: Wittig reaction;

DOI:10.1021/ol990885n

Reference yield:

ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate (82614-10-6) → (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 (441352-41-6)

Guidance literature:

Multi-step reaction with 21 steps

1.1: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2.1: 100 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

3.1: hydrogen / Pd(OH)2/C / ethyl acetate; methanol / 20 °C

4.1: CSA / dimethylformamide; CH₂Cl₂ / 20 °C

5.1: NaHMDS; Bu₄NI / dimethylformamide / 0 °C

6.1: CSA; MeOH / CH₂Cl₂ / 20 °C

7.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

8.1: DIBAL-H / CH₂Cl₂ / -78 °C

9.1: i-Pr₂NEt; Bu₄NI / CH₂Cl₂ / 0 °C

10.1: CSA; MeOH / CH₂Cl₂ / 0 °C

11.1: 100 percent / I₂; imidazole; PPh₃ / benzene / 20 °C

12.1: 96 percent / t-BuOK / tetrahydrofuran / 0 °C

13.1: tetrahydrofuran / 2 h / 60 °C

14.1: NaHCO₃ / Pd(PPh₃)4 / H₂O; tetrahydrofuran; dimethylformamide / 20 h / 50 °C

14.2: 243.1 mg / NaOH; aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

15.1: 2,3-dimethyl-2-butene; BH₃*THF / tetrahydrofuran / -20 - 0 °C

15.2: 73 percent / NaOH; aq. H₂O₂ / tetrahydrofuran / 2 h

16.1: (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

17.1: 55.4 mg / p-TsOH*H₂O / CH₂Cl₂ / 22 h / 20 - 55 °C

18.1: SO₃*pyridine complex; triethylamine; DMSO / CH₂Cl₂ / 0 - 20 °C

19.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

19.2: 39.3 mg / tetrahydrofuran; CH₂Cl₂ / 1 h / 0 °C

20.1: 86 percent / BF₃*Et₂O; Et₃SiH / acetonitrile; CH₂Cl₂ / 0 - 20 °C

21.1: iodine / CH₂Cl₂ / 0 - 20 °C

21.2: 17.7 mg / zinc; acetic acid / diethyl ether; methanol / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; methanol; triethylsilane; dmap; 2,3-Dimethyl-2-butene; borane-THF; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; iodine; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; benzene; 14.1: Suzuki cross-coupling / 16.1: Swern oxidation / 19.2: Wittig reaction;

DOI:10.1021/ol990885n

upstream 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

C₁₇H₂₀O₆

2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)ethanol

ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate

Downstream raw materials:

(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