C₃₈H₅₁N₃SO₈C₂H₄O

Base Information

• Chemical Name: C₃₈H₅₁N₃SO₈C₂H₄O
• CAS No.: 286372-63-2
• Molecular Formula: C₄₀H₅₅N₃O₉S
• Molecular Weight: 753.957
• Mol file: 286372-63-2.mol

Synonyms:C₃₈H₅₁N₃SO₈C₂H₄O

Chemical Property of C₃₈H₅₁N₃SO₈C₂H₄O

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₃₈H₅₁N₃SO₈C₂H₄O

There total 45 articles about C₃₈H₅₁N₃SO₈C₂H₄O 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:

(3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol (168777-81-9) → C38H51N3SO8C2H4O (286372-63-2)

Guidance literature:

Multi-step reaction with 31 steps

1.1: O₃

1.2: 92 percent / PPh₃

2.1: t-BuLi / diethyl ether

3.1: K₂CO₃; MeOH

4.1: MnO₂ / CH₂Cl₂

5.1: Me₄NBH(OAc)3

6.1: 91 percent / aq. NaOH; DMPU

7.1: 100 percent / TBAF

8.1: PPh₃; DEAD

9.1: aq. H₂O₂; (NH₄)6Mo₇O₂₄*4H₂O

10.1: 85 percent / KHMDS / tetrahydrofuran; toluene / -78 - 20 °C

11.1: 93 percent / DIBAL / CH₂Cl₂; hexane / 0.17 h / -78 °C

12.1: 78 percent / 2,6-lutidine; LiCl; MeSO₂Cl / dimethylformamide / 1 h / 20 °C

13.1: NaI; 2,6-di(tert-butyl)-4-methylpyridine / acetone

14.1: NaHMDS

15.1: Na/Hg

16.1: SiO₂ / CHCl₃

17.1: TBAF; AcOH / 0 °C

18.1: 88 percent / TBAF

19.1: Py-SO₃ / dimethylsulfoxide

20.1: aq. NaClO₂

21.1: dimedone / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

22.1: 4.2 mg / Et₃N; 2-chloro-1-methylpyridinium iodide / tetrahydrofuran; toluene / 1 h

23.1: 90 percent / camphorsulfonic acid / methanol / 0.25 h

24.1: DMAP / tetrahydrofuran / -78 °C

25.1: Et₂NH / tetrahydrofuran

26.1: BOP; Et₃N / tetrahydrofuran

With 2,6-dimethylpyridine; methanol; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; manganese(IV) oxide; ammonium heptamolybdate; sodium hydroxide; sodium chlorite; sodium amalgam; 2,6-di-tert-butyl-4-methylpyridine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; tert.-butyl lithium; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; silica gel; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimedone; ozone; acetic acid; methanesulfonyl chloride; diethylamine; triethylamine; triphenylphosphine; sodium iodide; lithium chloride; tetramethylammonium triacetoxyborohydride; diethylazodicarboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; 11.1: Mitsunobu reaction / 24.1: Parikh-Doering oxidation;

DOI:10.1021/ol991049g

Reference yield:

(Z)-3-{(4R,5S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-but-2-en-1-ol (171013-64-2) → C38H51N3SO8C2H4O (286372-63-2)

Guidance literature:

Multi-step reaction with 23 steps

1: 100 percent / TBAF

2: PPh₃; DEAD

3: aq. H₂O₂; (NH₄)6Mo₇O₂₄*4H₂O

4: 85 percent / KHMDS / tetrahydrofuran; toluene / -78 - 20 °C

5: 93 percent / DIBAL / CH₂Cl₂; hexane / 0.17 h / -78 °C

6: 78 percent / 2,6-lutidine; LiCl; MeSO₂Cl / dimethylformamide / 1 h / 20 °C

7: NaI; 2,6-di(tert-butyl)-4-methylpyridine / acetone

8: NaHMDS

9: Na/Hg

10: SiO₂ / CHCl₃

11: TBAF; AcOH / 0 °C

12: 88 percent / TBAF

13: Py-SO₃ / dimethylsulfoxide

14: aq. NaClO₂

15: dimedone / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

16: 4.2 mg / Et₃N; 2-chloro-1-methylpyridinium iodide / tetrahydrofuran; toluene / 1 h

17: 90 percent / camphorsulfonic acid / methanol / 0.25 h

18: DMAP / tetrahydrofuran / -78 °C

19: Et₂NH / tetrahydrofuran

20: BOP; Et₃N / tetrahydrofuran

With 2,6-dimethylpyridine; dmap; ammonium heptamolybdate; sodium chlorite; sodium amalgam; 2,6-di-tert-butyl-4-methylpyridine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; silica gel; potassium hexamethylsilazane; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimedone; acetic acid; methanesulfonyl chloride; diethylamine; triethylamine; triphenylphosphine; sodium iodide; lithium chloride; diethylazodicarboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; 3: Mitsunobu reaction / 16: Parikh-Doering oxidation;

DOI:10.1021/ol991049g

Reference yield:

methyl 2-fluoro-6-methoxybenzoate (178747-79-0) → C38H51N3SO8C2H4O (286372-63-2)

Guidance literature:

Multi-step reaction with 24 steps

1: 95 percent / NO₂BF₄

2: SnCl₂; aq. HCl

3: 60 percent / LiBEt₃H; 15-crown-5 / tetrahydrofuran

4: DMAP

5: NaI

6: 85 percent / BBr₃ / CH₂Cl₂

7: 100 percent / dimethylformamide

8: NaHMDS

9: Na/Hg

10: SiO₂ / CHCl₃

11: TBAF; AcOH / 0 °C

12: 88 percent / TBAF

13: Py-SO₃ / dimethylsulfoxide

14: aq. NaClO₂

15: dimedone / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

16: 4.2 mg / Et₃N; 2-chloro-1-methylpyridinium iodide / tetrahydrofuran; toluene / 1 h

17: 90 percent / camphorsulfonic acid / methanol / 0.25 h

18: DMAP / tetrahydrofuran / -78 °C

19: Et₂NH / tetrahydrofuran

20: BOP; Et₃N / tetrahydrofuran

With hydrogenchloride; dmap; sodium chlorite; sodium amalgam; nitronium tetrafluoborate; 15-crown-5; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; silica gel; boron tribromide; lithium triethylborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimedone; acetic acid; diethylamine; triethylamine; sodium iodide; tin(ll) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 17: Parikh-Doering oxidation;

DOI:10.1021/ol991049g

upstream raw materials:

Cyclohexanecarboxylic acid

C₃₁H₄₁N₃SO₇C₂H₄OC₁₅H₁₀O₂

(3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol

(Z)-3-{(4R,5S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-but-2-en-1-ol

Downstream raw materials:

(+)-thiazinotrienomycin E