(2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-3-ol

Base Information

• Chemical Name: (2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-3-ol
• CAS No.: 725253-61-2
• Molecular Formula: C₅₄H₆₈O₁₂
• Molecular Weight: 909.127

Synonyms:(2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-3-ol

Chemical Property of (2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-3-ol

Chemical Property:

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Technology Process of (2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-3-ol

There total 18 articles about (2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-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: 78.0%

8-benzyloxy-6-(8-benzyloxy-7-benzyloxymethyl-5,5a,7,8,9,10,11,11a-octahydro-4H-1,6-dioxa-cycloheptacycloocten-2-ylmethyl)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene (725253-48-5) → (2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-3-ol (725253-61-2)

Guidance literature:

8-benzyloxy-6-(8-benzyloxy-7-benzyloxymethyl-5,5a,7,8,9,10,11,11a-octahydro-4H-1,6-dioxa-cycloheptacycloocten-2-ylmethyl)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene; With thexylborane; In tetrahydrofuran; at 0 ℃;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2004.04.083

Reference yield:

(2R,3R,4S,4aS,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,9,9a-hexahydro-6H-pyrano[3,2-b]oxepin (252046-22-3) → (2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-3-ol (725253-61-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: AD-mix β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 0 °C

2.1: CSA / CH₂Cl₂ / 20 °C

3.1: H₂ / Pd/C / ethyl acetate; methanol / 20 °C

4.1: CSA / CH₂Cl₂ / 20 °C

5.1: 92 percent / KOt-Bu; n-Bu₄NI / tetrahydrofuran / 20 °C

6.1: 100 percent / DIBAL-H / CH₂Cl₂ / -78 - 0 °C

7.1: 92 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 20 °C

8.1: 99 percent / NaH / dimethylformamide / 0 - 20 °C

9.1: 9-BBN / tetrahydrofuran / 20 °C

9.2: aq. Cs₂CO₃ / PdCl₂(dppf)*CH₂Cl₂ / tetrahydrofuran; dimethylformamide / 50 °C

10.1: thexylborane / tetrahydrofuran / 0 °C

10.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 20 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; methanesulfonamide; thexylborane; camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 9.1: Suzuki-Miyaura coupling / 9.2: Suzuki-Miyaura coupling;

DOI:10.1016/j.tetlet.2004.04.083

Reference yield:

(3aS,4aS,6R,7R,8R,8aS,10aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene (725253-39-4) → (2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-decahydro-1,6-dioxa-cycloheptacycloocten-3-ol (725253-61-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: H₂ / Pd/C / ethyl acetate; methanol / 20 °C

2.1: CSA / CH₂Cl₂ / 20 °C

3.1: 92 percent / KOt-Bu; n-Bu₄NI / tetrahydrofuran / 20 °C

4.1: 100 percent / DIBAL-H / CH₂Cl₂ / -78 - 0 °C

5.1: 92 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 20 °C

6.1: 99 percent / NaH / dimethylformamide / 0 - 20 °C

7.1: 9-BBN / tetrahydrofuran / 20 °C

7.2: aq. Cs₂CO₃ / PdCl₂(dppf)*CH₂Cl₂ / tetrahydrofuran; dimethylformamide / 50 °C

8.1: thexylborane / tetrahydrofuran / 0 °C

8.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 20 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; thexylborane; camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 7.1: Suzuki-Miyaura coupling / 7.2: Suzuki-Miyaura coupling;

DOI:10.1016/j.tetlet.2004.04.083

upstream raw materials:

8-benzyloxy-6-(8-benzyloxy-7-benzyloxymethyl-5,5a,7,8,9,10,11,11a-octahydro-4H-1,6-dioxa-cycloheptacycloocten-2-ylmethyl)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene

p-Anisaldehyde dimethyl acetal

(2R,3R,4S,4aS,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,9,9a-hexahydro-6H-pyrano[3,2-b]oxepin

(3aS,4aS,5aR,8R,9aS,10R,10aR,12aR)-8-(4-Methoxy-phenyl)-2,2-dimethyl-decahydro-1,3,5,7,9,11-hexaoxa-naphtho[2,3-f]azulen-10-ol

Downstream raw materials:

(2S,5aS,7R,8S,11aR)-8-Benzyloxy-2-[(3aS,4aS,6R,7R,8S,8aS,10aR)-8-benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-ylmethyl]-7-benzyloxymethyl-octahydro-1,6-dioxa-cycloheptacycloocten-3-one

C₅₃H₇₆O₁₁Si₂

C₄₆H₅₆O₁₀

C₄₁H₄₆O₉

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