(2S,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2-iodomethyl-3-(4-methoxy-benzyloxy)-9-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Base Information

Chemical Name:(2S,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2-iodomethyl-3-(4-methoxy-benzyloxy)-9-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene
CAS No.:436153-52-5
Molecular Formula:C₃₉H₄₉IO₇
Molecular Weight:756.718
Hs Code.:

(2S,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2-iodomethyl-3-(4-methoxy-benzyloxy)-9-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Synonyms:(2S,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2-iodomethyl-3-(4-methoxy-benzyloxy)-9-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Suppliers and Price of (2S,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2-iodomethyl-3-(4-methoxy-benzyloxy)-9-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (2S,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2-iodomethyl-3-(4-methoxy-benzyloxy)-9-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (2S,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2-iodomethyl-3-(4-methoxy-benzyloxy)-9-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

There total 52 articles about (2S,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2-iodomethyl-3-(4-methoxy-benzyloxy)-9-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene 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: 92.0%

: 436153-90-1
[(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-3-(4-methoxy-benzyloxy)-9-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-methanol

: 436153-52-5
(2S,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2-iodomethyl-3-(4-methoxy-benzyloxy)-9-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In benzene; at 20 ℃; for 0.5h;
DOI:10.1021/ol025814u

Reference yield:

: (5R,6S)-5,9-Bis-benzyloxy-6-methoxymethoxy-6-methyl-nonanal

: 436153-52-5
(2S,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2-iodomethyl-3-(4-methoxy-benzyloxy)-9-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Guidance literature:: Multi-step reaction with 12 steps

1.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

2.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 2 h / 20 °C

2.2: 62 percent / DMAP / toluene; tetrahydrofuran / Heating

3.1: KHMDS; hexamethylphosphoramide / tetrahydrofuran; toluene / 0.75 h / -78 °C

4.1: 9-BBN / tetrahydrofuran / 2 h / 20 °C

4.2: 15.73 g / PdCl₂(dppf)*CH₂Cl₂; aq. Cs₂CO₃ / dimethylformamide; tetrahydrofuran / 13.5 h / 50 °C

5.1: BH₃*SMe₂ / tetrahydrofuran / 4.5 h / 20 °C

5.2: 33 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 2.5 h / 20 °C

6.1: 85 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine-N-oxide; 4A molecular sieves / acetonitrile / 2.5 h / 20 °C

7.1: 51 percent / DBU / toluene / 12 h / 110 °C

8.1: 74 percent / Zn(OTf)2 / CH₂Cl₂ / 15.5 h / 20 °C

9.1: camphorsulphonic acid / CH₂Cl₂ / 4.5 h / 20 °C

10.1: AIBN; Ph₃SnH / toluene / 3.5 h / 100 °C

11.1: 4.37 g / DIBALH / CH₂Cl₂; hexane / -78 - 0 °C

12.1: 89 percent / I₂; PPh₃; imidazole / benzene / 0.5 h / 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; triphenylstannane; iodine; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; benzene; 4.2: Suzuki-Miyaura cross-coupling;
DOI:10.1021/ja042686r

Reference yield:

: 436153-62-7
(5R,6S)-1-(tert-Butyl-dimethyl-silanyloxy)-6-methoxymethoxy-6,10-dimethyl-undec-9-en-5-ol

: 436153-52-5
(2S,3S,4aR,5aS,8R,9S,10aR,11aS)-8-Benzyloxy-9-(3-benzyloxy-propyl)-2-iodomethyl-3-(4-methoxy-benzyloxy)-9-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

Guidance literature:: Multi-step reaction with 19 steps

1.1: 7.93 g / potassium t-butoxide / tetrahydrofuran / 0 - 20 °C

2.1: N-methylmorpholine-N-oxide; aq. OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 72 h / 20 °C

3.1: aq. NaIO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 20 °C

4.1: 5.67 g / NaBH₄ / methanol / 0.5 h / 0 °C

5.1: potassium t-butoxide / tetrahydrofuran / 0 - 20 °C

6.1: 5.23 g / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

7.1: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 1.5 h / 0 °C

8.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 2 h / 20 °C

9.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 2 h / 20 °C

9.2: 62 percent / DMAP / toluene; tetrahydrofuran / Heating

10.1: KHMDS; hexamethylphosphoramide / tetrahydrofuran; toluene / 0.75 h / -78 °C

11.1: 9-BBN / tetrahydrofuran / 2 h / 20 °C

11.2: 15.73 g / PdCl₂(dppf)*CH₂Cl₂; aq. Cs₂CO₃ / dimethylformamide; tetrahydrofuran / 13.5 h / 50 °C

12.1: BH₃*SMe₂ / tetrahydrofuran / 4.5 h / 20 °C

12.2: 33 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 2.5 h / 20 °C

13.1: 85 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine-N-oxide; 4A molecular sieves / acetonitrile / 2.5 h / 20 °C

14.1: 51 percent / DBU / toluene / 12 h / 110 °C

15.1: 74 percent / Zn(OTf)2 / CH₂Cl₂ / 15.5 h / 20 °C

16.1: camphorsulphonic acid / CH₂Cl₂ / 4.5 h / 20 °C

17.1: AIBN; Ph₃SnH / toluene / 3.5 h / 100 °C

18.1: 4.37 g / DIBALH / CH₂Cl₂; hexane / -78 - 0 °C

19.1: 89 percent / I₂; PPh₃; imidazole / benzene / 0.5 h / 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; pyridine-SO₃ complex; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; triphenylstannane; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; benzene; 7.1: Swern oxidation / 11.2: Suzuki-Miyaura cross-coupling;
DOI:10.1021/ja042686r