Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-(2,5-dihydroxy-pentyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

Base Information

• Chemical Name: Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-(2,5-dihydroxy-pentyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester
• CAS No.: 218965-73-2
• Molecular Formula: C₃₃H₄₉NO₁₁
• Molecular Weight: 635.752
• Mol file: 218965-73-2.mol

Synonyms:

Chemical Property of Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-(2,5-dihydroxy-pentyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-(2,5-dihydroxy-pentyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

There total 23 articles about Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-(2,5-dihydroxy-pentyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester 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:

1-chloro-3-hydroxypropane (627-30-5) + Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester (218965-72-1) → Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-(2,5-dihydroxy-pentyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester (218965-73-2)

Guidance literature:

1-chloro-3-hydroxypropane; With methylmagnesium chloride; magnesium; ethylene dibromide; In tetrahydrofuran; for 3h; Heating;

Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1039/a909898d

Reference yield:

3-chloromagnesiumpropan-1-olate magnesium chloride (68236-10-2) + Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester (218965-72-1) → Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-(2,5-dihydroxy-pentyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester (218965-73-2)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1055/s-1998-1970

Reference yield:

(4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one (139403-50-2) → Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-(2,5-dihydroxy-pentyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester (218965-73-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 80 mg

2.1: LiBH(s-Bu)3 / tetrahydrofuran / 0.25 h / -95 °C

3.1: CSA / CH₂Cl₂ / 0.67 h / 20 °C

4.1: DMAP; DIPEA; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

5.1: hydroquinine 9-phenanthryl ether; potassium osmate dihydrate; aq. K₃Fe(CN)6 / 2-methyl-propan-2-ol / 8 h / 20 °C

6.1: aq. NaIO₄ / methanol / 1 h / 20 °C

7.1: 27 mg / Et₃N / toluene / 0.03 h / Heating

8.1: MeMgCl; Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating

8.2: 20 mg / tetrahydrofuran / 2 h / -78 °C

With dmap; potassium osmate(VI); sodium periodate; 4 A molecular sieve; camphor-10-sulfonic acid; methylmagnesium chloride; L-Selectride; magnesium; dihydroquinine 9-O-(9'-phenanthryl) ether; ethylene dibromide; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol; 2.1: Reduction / 3.1: Addition / 4.1: Acylation / 5.1: Oxidation / 6.1: Oxidation / 7.1: Elimination / 8.1: Metallation / 8.2: Grignard reaction;

DOI:10.1039/a909898d

upstream raw materials:

3-chloromagnesiumpropan-1-olate magnesium chloride

Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester

1-chloro-3-hydroxypropane

(4R,5R,6R)-5,6-Dimethyl-4-(phenylselanylmethyl)tetrahydro-2H-pyran-2-one

Downstream raw materials:

17-epi-7-O-Benzoyltheopederin D

7-O-Benzoyltheopederin D