{(2R,3R,5S,6S)-2,5-Dimethyl-6-[(E)-3-methyl-4-(toluene-4-sulfonyl)-but-2-enyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(2R,3R,5S,6S)-2,5-Dimethyl-6-[(E)-3-methyl-4-(toluene-4-sulfonyl)-but-2-enyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester
• CAS No.: 263881-11-4
• Molecular Formula: C₂₄H₃₇NO₅S
• Molecular Weight: 451.627

Synonyms:{(2R,3R,5S,6S)-2,5-Dimethyl-6-[(E)-3-methyl-4-(toluene-4-sulfonyl)-but-2-enyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester

Chemical Property of {(2R,3R,5S,6S)-2,5-Dimethyl-6-[(E)-3-methyl-4-(toluene-4-sulfonyl)-but-2-enyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2R,3R,5S,6S)-2,5-Dimethyl-6-[(E)-3-methyl-4-(toluene-4-sulfonyl)-but-2-enyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester

There total 12 articles about {(2R,3R,5S,6S)-2,5-Dimethyl-6-[(E)-3-methyl-4-(toluene-4-sulfonyl)-but-2-enyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl 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: 87.0%

sodium 4-methylbenzenesulfinate (824-79-3) + [(2R,3R,5S,6S)-6-((E)-4-Bromo-3-methyl-but-2-enyl)-2,5-dimethyl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester (263881-10-3) → {(2R,3R,5S,6S)-2,5-Dimethyl-6-[(E)-3-methyl-4-(toluene-4-sulfonyl)-but-2-enyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (263881-11-4)

Guidance literature:

In N,N-dimethyl-formamide; for 17h;

DOI:10.1016/S0040-4039(01)01763-4

Reference yield:

(4S,5R)-3-(tert-Butoxycarbonyl)-4-formyl-2,2,5-trimethyloxazolidine (108149-62-8) → {(2R,3R,5S,6S)-2,5-Dimethyl-6-[(E)-3-methyl-4-(toluene-4-sulfonyl)-but-2-enyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (263881-11-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 95 percent / benzene / Heating

2.1: 100 percent / H₂ / Pd(OH)2/C / propan-2-ol / 6 h

3.1: CSA / methanol / 12 h

3.2: CSA / benzene

4.1: 65 percent / Lawesson's reagent / toluene / 7 h / 80 °C

5.1: 81 percent / toluene / 24 h / 80 °C

6.1: 100 percent / DBU / benzene / 6 h / Heating

7.1: 68 percent / H₂ / PtO₂ / acetic acid / 24 h / 3040 Torr

8.1: 94 percent / DIBAL / toluene / -70 °C

9.1: 97 percent / benzene / 6 h / Heating

10.1: 82 percent / DIBAL / toluene / -78 - 20 °C

11.1: 90 percent / CBr₄; PPh₃ / CH₂Cl₂

12.1: 87 percent / dimethylformamide / 17 h

With Lawessons reagent; carbon tetrabromide; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; platinum(IV) oxide; palladium dihydroxide; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol; toluene; benzene; 1.1: Wittig reaction / 5.1: Wittig reaction / 9.1: Wittig reaction;

DOI:10.1016/S0040-4039(01)01763-4

Reference yield:

(4R,5R)-4-t-butoxycarbonylamino-2-methylhexan-5-olide (263881-01-2) → {(2R,3R,5S,6S)-2,5-Dimethyl-6-[(E)-3-methyl-4-(toluene-4-sulfonyl)-but-2-enyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (263881-11-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 65 percent / Lawesson's reagent / toluene / 7 h / 80 °C

2: 81 percent / toluene / 24 h / 80 °C

3: 100 percent / DBU / benzene / 6 h / Heating

4: 68 percent / H₂ / PtO₂ / acetic acid / 24 h / 3040 Torr

5: 94 percent / DIBAL / toluene / -70 °C

6: 97 percent / benzene / 6 h / Heating

7: 82 percent / DIBAL / toluene / -78 - 20 °C

8: 90 percent / CBr₄; PPh₃ / CH₂Cl₂

9: 87 percent / dimethylformamide / 17 h

With Lawessons reagent; carbon tetrabromide; hydrogen; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; platinum(IV) oxide; In dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene; benzene; 2: Wittig reaction / 6: Wittig reaction;

DOI:10.1016/S0040-4039(01)01763-4

upstream raw materials:

sodium 4-methylbenzenesulfinate

[(2R,3R,5S,6S)-6-((E)-4-Bromo-3-methyl-but-2-enyl)-2,5-dimethyl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

(4S,5R)-3-(tert-Butoxycarbonyl)-4-formyl-2,2,5-trimethyloxazolidine

(4R,5R)-4-t-butoxycarbonylamino-2-methylhexan-5-olide

Downstream raw materials:

4-(tert-butyl-diphenyl-silanyloxy)-pent-2-enoic acid (6-{5-[3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-6-methyl-4-methylene-tetrahydro-pyran-2-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide

(Z)-(S)-4-(tert-Butyl-diphenyl-silanyloxy)-pent-2-enoic acid {(2R,3R,5S,6S)-2,5-dimethyl-6-[(E)-3-methyl-4-(toluene-4-sulfonyl)-but-2-enyl]-tetrahydro-pyran-3-yl}-amide

(2R,3R,5S,6S)-2,5-Dimethyl-6-[(E)-3-methyl-4-(toluene-4-sulfonyl)-but-2-enyl]-tetrahydro-pyran-3-ylamine

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