(2S,2'R,5'S,2''R,3''S,5''R)-5''-((2S,3S,5R,6R)-6-Benzyloxymethyl-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-5-bromomethyl-5'-ethyl-2,5,3''-trimethyl-dodecahydro-[2,2';5',2'']terfuran

Base Information

• Chemical Name: (2S,2'R,5'S,2''R,3''S,5''R)-5''-((2S,3S,5R,6R)-6-Benzyloxymethyl-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-5-bromomethyl-5'-ethyl-2,5,3''-trimethyl-dodecahydro-[2,2';5',2'']terfuran
• CAS No.: 73992-27-5
• Molecular Formula: C₃₄H₅₃BrO₆
• Molecular Weight: 637.695
• Mol file: 73992-27-5.mol

Synonyms:(2S,2'R,5'S,2''R,3''S,5''R)-5''-((2S,3S,5R,6R)-6-Benzyloxymethyl-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-5-bromomethyl-5'-ethyl-2,5,3''-trimethyl-dodecahydro-[2,2';5',2'']terfuran

Chemical Property of (2S,2'R,5'S,2''R,3''S,5''R)-5''-((2S,3S,5R,6R)-6-Benzyloxymethyl-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-5-bromomethyl-5'-ethyl-2,5,3''-trimethyl-dodecahydro-[2,2';5',2'']terfuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,2'R,5'S,2''R,3''S,5''R)-5''-((2S,3S,5R,6R)-6-Benzyloxymethyl-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-5-bromomethyl-5'-ethyl-2,5,3''-trimethyl-dodecahydro-[2,2';5',2'']terfuran

There total 7 articles about (2S,2'R,5'S,2''R,3''S,5''R)-5''-((2S,3S,5R,6R)-6-Benzyloxymethyl-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-5-bromomethyl-5'-ethyl-2,5,3''-trimethyl-dodecahydro-[2,2';5',2'']terfuran 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:

(2S,3S)-3-(2-Bromo-ethyl)-2-methyl-2-(3-methyl-but-3-enyl)-1,4-dioxa-spiro[4.4]nonane (73991-89-6) → (2S,2'R,5'S,2''R,3''S,5''R)-5''-((2S,3S,5R,6R)-6-Benzyloxymethyl-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-5-bromomethyl-5'-ethyl-2,5,3''-trimethyl-dodecahydro-[2,2';5',2'']terfuran (73992-27-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) Mg, 2.) CuI, Bu₃P / 2) THF, -78 deg C

2: 70 percent / tetrahydrofuran / -78 °C

3: NBS, p-TsOH / CH₂Cl₂ / 0 °C

4: Et₃N / CH₂Cl₂ / 0 °C

5: NaOAc, trifluoroethanol / 60 °C

6: 2.) p-TsOH / 1) THF, -78 deg C; 2) CH₃OH

With N-Bromosuccinimide; copper(l) iodide; 2,2,2-trifluoroethanol; tributylphosphine; sodium acetate; toluene-4-sulfonic acid; magnesium; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00526a075

Reference yield:

(2R,3S,5R)-5-((2S,3S,5R)-3,5-Dimethyl-6-oxo-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-carbothioic acid S-pyridin-2-yl ester (73991-90-9) → (2S,2'R,5'S,2''R,3''S,5''R)-5''-((2S,3S,5R,6R)-6-Benzyloxymethyl-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-5-bromomethyl-5'-ethyl-2,5,3''-trimethyl-dodecahydro-[2,2';5',2'']terfuran (73992-27-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) Mg, 2.) CuI, Bu₃P / 2) THF, -78 deg C

2: 70 percent / tetrahydrofuran / -78 °C

3: NBS, p-TsOH / CH₂Cl₂ / 0 °C

4: Et₃N / CH₂Cl₂ / 0 °C

5: NaOAc, trifluoroethanol / 60 °C

6: 2.) p-TsOH / 1) THF, -78 deg C; 2) CH₃OH

With N-Bromosuccinimide; copper(l) iodide; 2,2,2-trifluoroethanol; tributylphosphine; sodium acetate; toluene-4-sulfonic acid; magnesium; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00526a075

Reference yield:

(3R,5S,6S)-6-{(2R,4S,5R)-5-[(1S,4S)-4-((S)-5-Bromomethyl-2,5-dimethyl-tetrahydro-furan-2-yl)-1-ethyl-1,4-dihydroxy-butyl]-4-methyl-tetrahydro-furan-2-yl}-3,5-dimethyl-tetrahydro-pyran-2-one (73992-28-6) → (2S,2'R,5'S,2''R,3''S,5''R)-5''-((2S,3S,5R,6R)-6-Benzyloxymethyl-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-5-bromomethyl-5'-ethyl-2,5,3''-trimethyl-dodecahydro-[2,2';5',2'']terfuran (73992-27-5)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂ / 0 °C

2: NaOAc, trifluoroethanol / 60 °C

3: 2.) p-TsOH / 1) THF, -78 deg C; 2) CH₃OH

With 2,2,2-trifluoroethanol; sodium acetate; toluene-4-sulfonic acid; triethylamine; In dichloromethane;

DOI:10.1021/ja00526a075

upstream raw materials:

benzyloxymethyl lithium

(3R,5S,6S)-6-((2R,3S,5R,2'S,5'R,2''S)-5''-Bromomethyl-2'-ethyl-3,2'',5''-trimethyl-dodecahydro-[2,2';5',2'']terfuran-5-yl)-3,5-dimethyl-tetrahydro-pyran-2-one

trimethyl orthoformate

(2S,3S)-3-(2-Bromo-ethyl)-2-methyl-2-(3-methyl-but-3-enyl)-1,4-dioxa-spiro[4.4]nonane

Downstream raw materials:

(S)-5-[(2S,5R,2'R,3'S,5'R)-5'-((2S,3S,5R,6R)-6-Benzyloxymethyl-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-2-ethyl-3'-methyl-octahydro-[2,2']bifuranyl-5-yl]-5-triethylsilanyloxy-hexan-2-one