[(3aS,4R,5R,6S,6aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-yl]-methanol

Base Information

• Chemical Name: [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-yl]-methanol
• CAS No.: 139573-30-1
• Molecular Formula: C₂₂H₃₆N₂O₄Si
• Molecular Weight: 420.624
• Mol file: 139573-30-1.mol

Synonyms:[(3aS,4R,5R,6S,6aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-yl]-methanol

Chemical Property of [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-yl]-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-yl]-methanol

There total 14 articles about [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-yl]-methanol 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: 86.0%

Toluene-4-sulfonic acid (3aR,4R,5R,6R,7R,7aR)-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-6-hydroxy-3a,4,5,6,7,7a-hexahydro-benzooxazol-7-yl ester (139582-59-5) → [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-yl]-methanol (139573-30-1)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at 65 ℃;

DOI:10.1016/S0040-4039(00)93444-0

Reference yield:

2-amino-4,6-O-benzylidene-3-O-(N-propylcarbamoyl)-2-deoxy-α-D-glucopyranoside (99679-74-0) → [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-yl]-methanol (139573-30-1)

Guidance literature:

Multi-step reaction with 13 steps

1: BaO, Ba(OH)2 / dimethylformamide

2: KOH, MeOC₂H₄OH / methanol; dioxane

3: NEt₃ / CH₂Cl₂

4: aq. AcOH

5: N-iodosuccinimide, PPh₃ / tetrahydrofuran

6: 2,6-lutidine / CH₂Cl₂

7: 96 percent / t-BuOK / tetrahydrofuran

8: 1) HgSO₄, 5M H₂SO₄, 2) MsCl, pyridine / 1) acetone, 60 deg C

9: NaBH₄, CeCl₃*7H₂O / methanol

10: Ms₂O, NEt₃ / methanol / CH₂Cl₂

11: 92 percent / OsO₄, Me₃N->O / H₂O; 2-methyl-propan-2-ol

12: 86 percent / DMAP, pyridine / CH₂Cl₂

13: 86 percent / L-Selectride / tetrahydrofuran / 65 °C

With pyridine; 2,6-dimethylpyridine; dmap; barium dihydroxide; potassium hydroxide; sodium tetrahydroborate; N-iodo-succinimide; osmium(VIII) oxide; cerium(III) chloride; 2-methoxy-ethanol; trimethylamine-N-oxide; sulfuric acid; potassium tert-butylate; L-Selectride; mercury(II) sulfate; acetic acid; methanesulfonyl chloride; triethylamine; triphenylphosphine; barium(II) oxide; Methanesulfonic anhydride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)93444-0

Reference yield:

methyl 2-desoxy-2-(methoxycarbonylamino)-α-D-glucopyranoside (34299-66-6) → [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-yl]-methanol (139573-30-1)

Guidance literature:

Multi-step reaction with 14 steps

1: pTsOH / dimethylformamide

2: BaO, Ba(OH)2 / dimethylformamide

3: KOH, MeOC₂H₄OH / methanol; dioxane

4: NEt₃ / CH₂Cl₂

5: aq. AcOH

6: N-iodosuccinimide, PPh₃ / tetrahydrofuran

7: 2,6-lutidine / CH₂Cl₂

8: 96 percent / t-BuOK / tetrahydrofuran

9: 1) HgSO₄, 5M H₂SO₄, 2) MsCl, pyridine / 1) acetone, 60 deg C

10: NaBH₄, CeCl₃*7H₂O / methanol

11: Ms₂O, NEt₃ / methanol / CH₂Cl₂

12: 92 percent / OsO₄, Me₃N->O / H₂O; 2-methyl-propan-2-ol

13: 86 percent / DMAP, pyridine / CH₂Cl₂

14: 86 percent / L-Selectride / tetrahydrofuran / 65 °C

With pyridine; 2,6-dimethylpyridine; dmap; barium dihydroxide; potassium hydroxide; sodium tetrahydroborate; N-iodo-succinimide; osmium(VIII) oxide; cerium(III) chloride; 2-methoxy-ethanol; trimethylamine-N-oxide; sulfuric acid; potassium tert-butylate; L-Selectride; toluene-4-sulfonic acid; mercury(II) sulfate; acetic acid; methanesulfonyl chloride; triethylamine; triphenylphosphine; barium(II) oxide; Methanesulfonic anhydride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)93444-0

upstream raw materials:

Toluene-4-sulfonic acid (3aR,4R,5R,6R,7R,7aR)-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-6-hydroxy-3a,4,5,6,7,7a-hexahydro-benzooxazol-7-yl ester

2-amino-4,6-O-benzylidene-3-O-(N-propylcarbamoyl)-2-deoxy-α-D-glucopyranoside

methyl 2-desoxy-2-(methoxycarbonylamino)-α-D-glucopyranoside

3-((2S,3R,4R,5S,6S)-4-Benzyloxy-5-hydroxy-6-iodomethyl-2-methoxy-tetrahydro-pyran-3-yl)-1,1-dimethyl-urea

Downstream raw materials:

[(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-dimethyl-amine

3-O-benzylallosamizoline

allosamidin

3,6-di-O-benzyl-(-)-allosamizoline