(2R,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2R,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester
• CAS No.: 114826-74-3
• Molecular Formula: C₂₉H₄₃NO₆Si
• Molecular Weight: 529.749
• Mol file: 114826-74-3.mol

Synonyms:(2R,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property of (2R,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester

There total 12 articles about (2R,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-methoxymethoxy-piperidine-1-carboxylic 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:

((3S,4R,5S,6S)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester → (2R,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester (114826-74-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 62 percent / ZnCl₂ / 4 h / Ambient temperature

2: 76 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 deg C upto RT

3: 96 percent / 1,2-dichloro-ethane / 2.5 h / Heating

4: 93 percent / Bu₃SnH / toluene / 2.5 h / Heating

5: 86 percent / NaOMe / methanol / 0.5 h / 0 °C

6: 95 percent / NaBH₄ / methanol; tetrahydrofuran / 0.5 h / 0 °C

7: 78 percent / BaO-Ba(OH)2*8H₂O / dimethylformamide / 40 h / Ambient temperature

8: 88 percent / 0.05M HCl / methanol / 0.67 h / Ambient temperature

9: 81 percent / P(Ph)3, CBr₄ / pyridine / 72 h / Ambient temperature

10: 93 percent / (Me₂CH)2NH / CH₂Cl₂; ethyl acetate / -10 deg C up to r.t., then 68 h at r.t.

11: KOC(CH₃)3 / tetrahydrofuran / 3 h / 0 °C

12: H₂/Pd (10percent on C) / ethanol / Ambient temperature

13: 94 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; barium dihydroxide; sodium tetrahydroborate; carbon tetrabromide; potassium tert-butylate; tri-n-butyl-tin hydride; sodium methylate; diisopropylamine; triphenylphosphine; zinc(II) chloride; barium(II) oxide; lithium diisopropyl amide; palladium on activated charcoal; hydrogen; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)96878-3

Reference yield:

((2R,4aS,7S,8aS)-6-Hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid tert-butyl ester (114826-67-4,114826-68-5) → (2R,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester (114826-74-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / NaBH₄ / methanol; tetrahydrofuran / 0.5 h / 0 °C

2: 78 percent / BaO-Ba(OH)2*8H₂O / dimethylformamide / 40 h / Ambient temperature

3: 88 percent / 0.05M HCl / methanol / 0.67 h / Ambient temperature

4: 81 percent / P(Ph)3, CBr₄ / pyridine / 72 h / Ambient temperature

5: 93 percent / (Me₂CH)2NH / CH₂Cl₂; ethyl acetate / -10 deg C up to r.t., then 68 h at r.t.

6: KOC(CH₃)3 / tetrahydrofuran / 3 h / 0 °C

7: H₂/Pd (10percent on C) / ethanol / Ambient temperature

8: 94 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; barium dihydroxide; sodium tetrahydroborate; carbon tetrabromide; potassium tert-butylate; diisopropylamine; triphenylphosphine; barium(II) oxide; palladium on activated charcoal; hydrogen; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)96878-3

Reference yield:

[1-Hydroxymethyl-2-((2R,4S,5S)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-ethyl]-carbamic acid tert-butyl ester (114826-69-6) → (2R,4S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester (114826-74-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 78 percent / BaO-Ba(OH)2*8H₂O / dimethylformamide / 40 h / Ambient temperature

2: 88 percent / 0.05M HCl / methanol / 0.67 h / Ambient temperature

3: 81 percent / P(Ph)3, CBr₄ / pyridine / 72 h / Ambient temperature

4: 93 percent / (Me₂CH)2NH / CH₂Cl₂; ethyl acetate / -10 deg C up to r.t., then 68 h at r.t.

5: KOC(CH₃)3 / tetrahydrofuran / 3 h / 0 °C

6: H₂/Pd (10percent on C) / ethanol / Ambient temperature

7: 94 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; barium dihydroxide; carbon tetrabromide; potassium tert-butylate; diisopropylamine; triphenylphosphine; barium(II) oxide; palladium on activated charcoal; hydrogen; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)96878-3

upstream raw materials:

[1-Hydroxymethyl-2-((2R,4S,5S)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-ethyl]-carbamic acid tert-butyl ester

((2R,4aS,7S,8aS)-6-Hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid tert-butyl ester

Benzoic acid (2R,4aS,6R,7S,8aS)-7-tert-butoxycarbonylamino-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester

Benzoic acid (2R,4aS,7S,8aS)-7-tert-butoxycarbonylamino-8-(imidazole-1-carbothioyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester

Downstream raw materials:

(2R,4S,5S)-acetamido-4-hydroxy-pipecolin acid