(2R,4aR,6S,7R,9S,10aS)-6-[(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-oxepan-2-ylmethyl]-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol

Base Information

• Chemical Name: (2R,4aR,6S,7R,9S,10aS)-6-[(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-oxepan-2-ylmethyl]-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol
• CAS No.: 342901-85-3
• Molecular Formula: C₅₂H₇₀O₉Si
• Molecular Weight: 867.208

Synonyms:(2R,4aR,6S,7R,9S,10aS)-6-[(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-oxepan-2-ylmethyl]-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol

Chemical Property of (2R,4aR,6S,7R,9S,10aS)-6-[(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-oxepan-2-ylmethyl]-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (2R,4aR,6S,7R,9S,10aS)-6-[(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-oxepan-2-ylmethyl]-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol

There total 23 articles about (2R,4aR,6S,7R,9S,10aS)-6-[(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-oxepan-2-ylmethyl]-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-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: 60.0%

[(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-2-((Z)-(2R,4aR,9S,10aS)-9-methyl-2-phenyl-4,4a,8,9,10,10a-hexahydro-1,3,5-trioxa-benzocycloocten-6-ylmethyl)-oxepan-3-yloxy]-tert-butyl-dimethyl-silane → (2R,4aR,6S,7R,9S,10aS)-6-[(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-oxepan-2-ylmethyl]-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol (342901-85-3)

Guidance literature:

[(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-2-((Z)-(2R,4aR,9S,10aS)-9-methyl-2-phenyl-4,4a,8,9,10,10a-hexahydro-1,3,5-trioxa-benzocycloocten-6-ylmethyl)-oxepan-3-yloxy]-tert-butyl-dimethyl-silane; With 3,3-dimethyldioxirane; In acetone; at -78 - -20 ℃;

With triethylsilane; borane-THF; In dichloromethane; at -20 ℃;

DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (2R,4aR,6S,7R,9S,10aS)-6-[(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-oxepan-2-ylmethyl]-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol (342901-85-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 61 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

2.1: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 20 °C

2.2: 70 percent / NaIO₄ / acetone; H₂O

3.1: 95 percent / NaClO₂; KH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 °C

4.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran

4.2: 83 percent / DMAP / benzene / Heating

5.1: 95 percent / KHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

6.1: 9-BBN / tetrahydrofuran / 20 °C

6.2: 85 percent / 1 M aq. NaHCO₃ / [Pd(PPh₃)4] / dimethylformamide / 50 °C

7.1: 3,3-dimethyldioxirane / acetone / -78 - -20 °C

7.2: 60 percent / Et₃SiH; BH₃*THF / CH₂Cl₂ / -20 °C

With sodium chlorite; potassium dihydrogenphosphate; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; 3,3-dimethyldioxirane; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; acetone; tert-butyl alcohol; 6.2: B-alkyl Suzuki coupling reaction;

DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

Reference yield:

benzyl bromide (100-39-0) → (2R,4aR,6S,7R,9S,10aS)-6-[(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-oxepan-2-ylmethyl]-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol (342901-85-3)

Guidance literature:

Multi-step reaction with 15 steps

1.1: n-Bu₂SnO / benzene / Heating

1.2: CsF / dimethylformamide / 20 °C

2.1: NaH; CS₂; MeI / tetrahydrofuran / 20 °C

2.2: n-Bu₃SnH; AIBN / benzene / Heating

3.1: conc. HCl / CHCl₃ / 20 °C

3.2: 46 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

4.1: 97 percent / N-methylmorpholine / CH₂Cl₂ / 20 °C

5.1: 98 percent / MeI; NaHCO₃ / acetonitrile; H₂O / 20 °C

6.1: SmI₂; HMPA / methanol; tetrahydrofuran / 0 °C

7.1: LiAlH₄ / tetrahydrofuran / 20 °C

8.1: 84 percent / NaH / dimethylformamide / 20 °C

9.1: 89 percent / camphorsulfonic acid / methanol / 20 °C

10.1: 2,6-lutidine / CH₂Cl₂ / 20 °C

11.1: camphorsulfonic acid / methanol / 0 °C

12.1: I₂; PPh₃; imidazole / tetrahydrofuran / 20 °C

13.1: t-BuOK / tetrahydrofuran / 20 °C

14.1: 9-BBN / tetrahydrofuran / 20 °C

14.2: 85 percent / 1 M aq. NaHCO₃ / [Pd(PPh₃)4] / dimethylformamide / 50 °C

15.1: 3,3-dimethyldioxirane / acetone / -78 - -20 °C

15.2: 60 percent / Et₃SiH; BH₃*THF / CH₂Cl₂ / -20 °C

With 4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; carbon disulfide; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; samarium diiodide; camphor-10-sulfonic acid; potassium tert-butylate; iodine; 3,3-dimethyldioxirane; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; triphenylphosphine; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; acetonitrile; benzene; 14.2: B-alkyl Suzuki coupling reaction;

DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

upstream raw materials:

benzaldehyde dimethyl acetal

benzyl bromide

(2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside

Downstream raw materials:

{(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9S,10aS)-7-(4-methoxy-benzyloxy)-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-6-ylmethyl]-oxepan-3-yloxy}-tert-butyl-dimethyl-silane

(2S,3R,5R,5aS,6aR,8R,10S,11R,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-11-hydroxymethyl-5a,8-dimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-ol

[(2S,3R,5R,5aS,6aR,8S,10S,12aS,13aR)-3,5-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5a,8-dimethyl-11-methylene-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-10-yloxy]-tert-butyl-dimethyl-silane

C₄₆H₅₄O₉

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