(+)-(2'R,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-1H-spiro[benzo[c]oxepine-3,2'-pyran]-3'-ol

Base Information

• Chemical Name: (+)-(2'R,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-1H-spiro[benzo[c]oxepine-3,2'-pyran]-3'-ol
• CAS No.: 1177259-25-4
• Molecular Formula: C₄₁H₆₀O₅Si₂
• Molecular Weight: 689.095
• Mol file: 1177259-25-4.mol

Synonyms:(+)-(2'R,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-1H-spiro[benzo[c]oxepine-3,2'-pyran]-3'-ol

Chemical Property of (+)-(2'R,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-1H-spiro[benzo[c]oxepine-3,2'-pyran]-3'-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2'R,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-1H-spiro[benzo[c]oxepine-3,2'-pyran]-3'-ol

There total 6 articles about (+)-(2'R,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-1H-spiro[benzo[c]oxepine-3,2'-pyran]-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: 54.0%

(-)-(2-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)ethyl)phenyl)methanol (1177258-96-6) → (+)-(2'S,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-1H-spiro[benzo[c]oxepine-3,2'-pyran]-3'-ol (1177259-07-2) + (+)-(2'R,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-1H-spiro[benzo[c]oxepine-3,2'-pyran]-3'-ol (1177259-25-4)

Guidance literature:

With 3,3-dimethyldioxirane; acetic acid; In dichloromethane; acetone; at -63 - -44 ℃; optical yield given as %de; stereoselective reaction;

DOI:10.1021/ol901437f

Reference yield:

(-)-(2R,4S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-iodo-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran (869336-47-0) → (+)-(2'S,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-1H-spiro[benzo[c]oxepine-3,2'-pyran]-3'-ol (1177259-07-2) + (+)-(2'R,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-1H-spiro[benzo[c]oxepine-3,2'-pyran]-3'-ol (1177259-25-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

1.2: 0.5 h / 20 °C / Inert atmosphere

1.3: 1 h / 20 °C / Inert atmosphere

2.1: methanol; potassium carbonate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

3.1: -78 - 20 °C

With methanol; potassium carbonate; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; 1.3: Suzuki-Miyaura coupling;

DOI:10.1021/ol901437f

Reference yield:

(-)-(2R,4S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-(tributylstannyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran → (+)-(2'S,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-1H-spiro[benzo[c]oxepine-3,2'-pyran]-3'-ol (1177259-07-2) + (+)-(2'R,3'R,4'S,6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-4'-(triisopropylsilyloxy)-3',4,4',5,5',6'-hexahydro-1H-spiro[benzo[c]oxepine-3,2'-pyran]-3'-ol (1177259-25-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: iodine / dichloromethane / 20 °C

2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

2.3: 1 h / 20 °C / Inert atmosphere

3.1: methanol; potassium carbonate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

4.1: -78 - 20 °C

With methanol; iodine; potassium carbonate; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane; 2.3: Suzuki-Miyaura coupling;

DOI:10.1021/ol901437f

upstream raw materials:

(-)-(2R,4S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-iodo-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran

(-)-(2-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)ethyl)phenyl)methanol

2-(vinyl)benzyl acetate

2-vinylbenzylalcohol