(S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester

Base Information

• Chemical Name: (S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester
• CAS No.: 185300-82-7
• Molecular Formula: C₂₁H₃₀O₇
• Molecular Weight: 394.465
• Mol file: 185300-82-7.mol

Synonyms:

Chemical Property of (S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester

There total 20 articles about (S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid 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: 71.0%

7-(3,4-dimethoxybenzyl)pederic acid (128271-10-3) + diazomethyl-trimethyl-silane (18107-18-1) → (S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester (185300-82-7)

Guidance literature:

In tetrahydrofuran; methanol; hexane;

DOI:10.1021/jo961841k

Reference yield:

(R)-3-((2S,3R)-3-Hydroxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one (104486-82-0) → (S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester (185300-82-7)

Guidance literature:

Multi-step reaction with 14 steps

1: 87 percent / triflic acid / cyclohexane; CH₂Cl₂ / 1 h

2: 1.) H₂O, LiBH₄, 2.) aq. NaOH / 1.) Et₂O, THF, 0 deg C - 1 h, 23 deg C - 1 h, 2.) Et₂O, THF, 23 deg C, 1 h

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C -> 0 deg C

4: 74 percent / TiCl₄ / CH₂Cl₂ / 16 h / -78 °C

5: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) 0 deg C, 30 min

6: 1.) 4-methylmorpholine N-oxide, OsO₄, 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, toluene, 1.5 h, 2.) t-BuOH, THF, H₂O, toluene, 30 min

7: 1.) Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min, 2.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min

8: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 -> 0 deg C

9: H₂ / Pd/C / methanol / 24 h / Ambient temperature

10: camphorsulfonic acid / methanol / 8 h

11: 1.) COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C -> 0 deg C

13: 82 percent / aq. H₂O₂, LiOH / tetrahydrofuran / 11 h / 23 °C

14: 71 percent / tetrahydrofuran; methanol; hexane

With 2,6-dimethylpyridine; lithium hydroxide; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium borohydride; oxalyl dichloride; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; water; hydrogen; dihydrogen peroxide; titanium tetrachloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane;

DOI:10.1021/jo961841k

Reference yield:

(3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate (905589-59-5) → (S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester (185300-82-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 36 h

2: 96 percent / aq. NaOH / tetrahydrofuran / 0.5 h

3: 1.) n-BuLi, 2.) oxalyl chloride / 1.) THF, hexanes, -78 deg C, 10 min, 2.) THF, hexanes, 23 deg C, 1 h

4: 62 percent / n-BuLi / tetrahydrofuran / 0.58 h / -78 °C

5: 1.) Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min, 2.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 -> 0 deg C

7: H₂ / Pd/C / methanol / 24 h / Ambient temperature

8: camphorsulfonic acid / methanol / 8 h

9: 1.) COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C -> 0 deg C

11: 82 percent / aq. H₂O₂, LiOH / tetrahydrofuran / 11 h / 23 °C

12: 71 percent / tetrahydrofuran; methanol; hexane

With lithium hydroxide; sodium hydroxide; n-butyllithium; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1021/jo961841k

upstream raw materials:

(+)-methyl pederate

4-chloromethyl-1,2-dimethoxy-benzene

7-(3,4-dimethoxybenzyl)pederic acid

diazomethyl-trimethyl-silane

Downstream raw materials:

(S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide

(S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-N-[(4R,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-yl]-acetamide

Acetic acid (S)-3-{(4S,4aS,6R,8S,8aR)-4-[(S)-2-(3,4-dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetylamino]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl}-2-methoxy-propyl ester

Acetic acid (S)-3-{(4R,4aS,6R,8S,8aR)-4-[(S)-2-(3,4-dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetylamino]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl}-2-methoxy-propyl ester