(2R,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7S,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-dihydro-pyran-3-one

Base Information

• Chemical Name: (2R,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7S,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-dihydro-pyran-3-one
• CAS No.: 315203-89-5
• Molecular Formula: C₄₄H₅₀O₉
• Molecular Weight: 722.876

Synonyms:(2R,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7S,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-dihydro-pyran-3-one

Chemical Property of (2R,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7S,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-dihydro-pyran-3-one

Chemical Property:

Purity/Quality:

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Technology Process of (2R,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7S,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-dihydro-pyran-3-one

There total 14 articles about (2R,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7S,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-dihydro-pyran-3-one 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: 94.0%

(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,7S,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-tetrahydro-pyran-3-ol → (2R,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7S,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-dihydro-pyran-3-one (315203-89-5)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(00)01483-0

Reference yield:

benzyl bromide (100-39-0) → (2R,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7S,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-dihydro-pyran-3-one (315203-89-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 97 percent / NaH; Bu₄NI / dimethylformamide / 20 °C

2.1: 9-BBN / tetrahydrofuran / 20 °C

2.2: 95 percent / H₂O₂; NaOH / 20 °C

3.1: 76 percent / KH; Bu₄NI / tetrahydrofuran / Heating

4.1: 86 percent / p-TsOH / methanol; CH₂Cl₂ / 20 °C

5.1: imidazole / dimethylformamide / 50 °C

6.1: CSA / methanol; CH₂Cl₂ / 0 °C

7.1: 95 percent / I₂; PPh₃; imidazole / benzene / 20 °C

8.1: 96 percent / t-BuOK / tetrahydrofuran / 0 °C

9.1: 9-BBN / tetrahydrofuran / 20 °C

9.2: 97 percent / aq. NaHCO₃; PdCl₂(1,1'-bis(diphenylphosphino)ferrocene / dimethylformamide / 24 h / 20 °C

10.1: BF₃*THF / tetrahydrofuran / -30 °C

10.2: 77 percent / H₂O₂; NaOH / 20 - 40 °C

11.1: 88 percent / KH; Bu₄NI / tetrahydrofuran / 20 °C

12.1: 100 percent / Bu₄NF / tetrahydrofuran / 20 °C

13.1: 94 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; tetrapropylammonium perruthennate; boron trifluoride-tetrahydrofuran complex; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 9.2: Suzuki coupling;

DOI:10.1016/S0040-4039(00)01483-0

Reference yield:

(2R,4aR,6S,7R,8aS)-2-Phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (315203-85-1) → (2R,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7S,9aS)-7-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-ylmethyl]-dihydro-pyran-3-one (315203-89-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 97 percent / NaH; Bu₄NI / dimethylformamide / 20 °C

2.1: 9-BBN / tetrahydrofuran / 20 °C

2.2: 95 percent / H₂O₂; NaOH / 20 °C

3.1: 76 percent / KH; Bu₄NI / tetrahydrofuran / Heating

4.1: 86 percent / p-TsOH / methanol; CH₂Cl₂ / 20 °C

5.1: imidazole / dimethylformamide / 50 °C

6.1: CSA / methanol; CH₂Cl₂ / 0 °C

7.1: 95 percent / I₂; PPh₃; imidazole / benzene / 20 °C

8.1: 96 percent / t-BuOK / tetrahydrofuran / 0 °C

9.1: 9-BBN / tetrahydrofuran / 20 °C

9.2: 97 percent / aq. NaHCO₃; PdCl₂(1,1'-bis(diphenylphosphino)ferrocene / dimethylformamide / 24 h / 20 °C

10.1: BF₃*THF / tetrahydrofuran / -30 °C

10.2: 77 percent / H₂O₂; NaOH / 20 - 40 °C

11.1: 88 percent / KH; Bu₄NI / tetrahydrofuran / 20 °C

12.1: 100 percent / Bu₄NF / tetrahydrofuran / 20 °C

13.1: 94 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; tetrapropylammonium perruthennate; boron trifluoride-tetrahydrofuran complex; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 9.2: Suzuki coupling;

DOI:10.1016/S0040-4039(00)01483-0

upstream raw materials:

benzyl bromide

(2R,4aR,6S,7R,8aS)-2-Phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

(2R,4aR,6S,7R,8aS)-7-Benzyloxy-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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

Downstream raw materials:

Toluene-4-sulfonic acid (4aR,5aS,6aR,8S,9S,10aS,11aR,13aS)-9-hydroxy-2,2,10a-trimethyl-8-(2-triisopropylsilanyloxy-ethyl)-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-ylmethyl ester

Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethanesulfonyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

Acetic acid (2S,3R,4aR,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-ethylsulfanyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

Acetic acid (2S,3R,4aS,5aR,8S,9R,10aS,11aR)-9-acetoxymethyl-3-benzyloxy-2-(2-benzyloxy-ethyl)-4a-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-yl ester

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