[(2R,3S,4aR,6S,7R,9aS)-7-[(2S,3S,4aR,8aS)-2-(2-Bromo-acetyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-1,5-dioxa-benzocyclohepten-6-yl]-acetaldehyde

Base Information

• Chemical Name: [(2R,3S,4aR,6S,7R,9aS)-7-[(2S,3S,4aR,8aS)-2-(2-Bromo-acetyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-1,5-dioxa-benzocyclohepten-6-yl]-acetaldehyde
• CAS No.: 256441-19-7
• Molecular Formula: C₅₄H₆₉BrO₉Si₂
• Molecular Weight: 998.211

Synonyms:[(2R,3S,4aR,6S,7R,9aS)-7-[(2S,3S,4aR,8aS)-2-(2-Bromo-acetyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-1,5-dioxa-benzocyclohepten-6-yl]-acetaldehyde

Chemical Property of [(2R,3S,4aR,6S,7R,9aS)-7-[(2S,3S,4aR,8aS)-2-(2-Bromo-acetyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-1,5-dioxa-benzocyclohepten-6-yl]-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3S,4aR,6S,7R,9aS)-7-[(2S,3S,4aR,8aS)-2-(2-Bromo-acetyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-1,5-dioxa-benzocyclohepten-6-yl]-acetaldehyde

There total 13 articles about [(2R,3S,4aR,6S,7R,9aS)-7-[(2S,3S,4aR,8aS)-2-(2-Bromo-acetyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-1,5-dioxa-benzocyclohepten-6-yl]-acetaldehyde 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:

2-bromo-1-{3-[3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2-hydroxy-ethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-yloxy]-octahydro-pyrano[3,2-b]pyran-2-yl}-ethanone (208454-54-0) → [(2R,3S,4aR,6S,7R,9aS)-7-[(2S,3S,4aR,8aS)-2-(2-Bromo-acetyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-1,5-dioxa-benzocyclohepten-6-yl]-acetaldehyde (256441-19-7)

Guidance literature:

With sulfur trioxide pyridine complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0 ℃; for 0.666667h;

DOI:10.1021/jo990989b

Reference yield:

((2R,3S)-3-Allyloxy-tetrahydro-pyran-2-yl)-acetaldehyde (208454-48-2) → [(2R,3S,4aR,6S,7R,9aS)-7-[(2S,3S,4aR,8aS)-2-(2-Bromo-acetyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-1,5-dioxa-benzocyclohepten-6-yl]-acetaldehyde (256441-19-7)

Guidance literature:

Multi-step reaction with 12 steps

2.1: sec-butyllithium / tetrahydrofuran / -78 °C

2.2: 32 percent / tetrahydrofuran / -78 °C

3.1: 29 percent / TiCl₄; triphenylphosphine / CH₂Cl₂ / -78 - 0 °C

4.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

5.1: N-methylmorpholine N-oxide; OsO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 20 °C

6.1: lead tetraacetate / benzene / 0.5 h / 20 °C

7.1: 2.778 g / tetrahydrofuran; diethyl ether / -78 - 0 °C

8.1: 94 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

9.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

9.2: tetrahydrofuran; hexane / 0.33 h / -78 °C

10.1: N-bromosuccinimide / tetrahydrofuran / 0.75 h / 0 °C

11.1: 101.0 mg / camphorsulfonic acid / CH₂Cl₂; methanol / 0 - 20 °C

12.1: triethylamine; sulfur trioxide-pyridine complex / CH₂Cl₂; dimethylsulfoxide / 0.67 h / 0 °C

With 2,6-dimethylpyridine; lead(IV) acetate; N-Bromosuccinimide; osmium(VIII) oxide; oxalyl dichloride; camphor-10-sulfonic acid; sec.-butyllithium; sulfur trioxide pyridine complex; titanium tetrachloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; benzene; 2.1: Metallation / 2.2: allylsilylation / 3.1: Cyclization / 4.1: Etherification / 5.1: Oxidation / 6.1: Oxidation / 7.1: Addition / 8.1: Oxidation / 9.1: Metallation / 9.2: Etherification / 10.1: Bromination / 11.1: Hydrolysis / 12.1: Oxidation;

DOI:10.1021/jo990989b

Reference yield:

(2R,3S,4aR,6S,7R,9aS)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2-hydroxy-ethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol (208454-47-1) → [(2R,3S,4aR,6S,7R,9aS)-7-[(2S,3S,4aR,8aS)-2-(2-Bromo-acetyl)-octahydro-pyrano[3,2-b]pyran-3-yloxy]-3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-1,5-dioxa-benzocyclohepten-6-yl]-acetaldehyde (256441-19-7)

Guidance literature:

Multi-step reaction with 12 steps

2.1: sec-butyllithium / tetrahydrofuran / -78 °C

2.2: 32 percent / tetrahydrofuran / -78 °C

3.1: 29 percent / TiCl₄; triphenylphosphine / CH₂Cl₂ / -78 - 0 °C

4.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

5.1: N-methylmorpholine N-oxide; OsO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 20 °C

6.1: lead tetraacetate / benzene / 0.5 h / 20 °C

7.1: 2.778 g / tetrahydrofuran; diethyl ether / -78 - 0 °C

8.1: 94 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

9.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

9.2: tetrahydrofuran; hexane / 0.33 h / -78 °C

10.1: N-bromosuccinimide / tetrahydrofuran / 0.75 h / 0 °C

11.1: 101.0 mg / camphorsulfonic acid / CH₂Cl₂; methanol / 0 - 20 °C

12.1: triethylamine; sulfur trioxide-pyridine complex / CH₂Cl₂; dimethylsulfoxide / 0.67 h / 0 °C

With 2,6-dimethylpyridine; lead(IV) acetate; N-Bromosuccinimide; osmium(VIII) oxide; oxalyl dichloride; camphor-10-sulfonic acid; sec.-butyllithium; sulfur trioxide pyridine complex; titanium tetrachloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; benzene; 2.1: Metallation / 2.2: allylsilylation / 3.1: Cyclization / 4.1: Etherification / 5.1: Oxidation / 6.1: Oxidation / 7.1: Addition / 8.1: Oxidation / 9.1: Metallation / 9.2: Etherification / 10.1: Bromination / 11.1: Hydrolysis / 12.1: Oxidation;

DOI:10.1021/jo990989b

upstream raw materials:

2-bromo-1-{3-[3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2-hydroxy-ethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-yloxy]-octahydro-pyrano[3,2-b]pyran-2-yl}-ethanone

((2R,3S)-3-Allyloxy-tetrahydro-pyran-2-yl)-acetaldehyde

(2R,3S,4aR,6S,7R,9aS)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2-hydroxy-ethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol

(2R,3S,4aR,5aS,9R,10aR,12aS)-9-((2R,3S)-3-Allyloxy-tetrahydro-pyran-2-ylmethyl)-3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-decahydro-1,5,8,10-tetraoxa-benzo[b]heptalene

Downstream raw materials:

C₄₀H₅₄O₉Si

C₄₀H₅₆O₉Si

C₄₄H₆₄O₈S₂Si

C₅₆H₇₄O₉Si₂

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