(R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butyric acid

Base Information

• Chemical Name: (R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butyric acid
• CAS No.: 887927-18-6
• Molecular Formula: C₃₁H₄₄O₆Si
• Molecular Weight: 540.772
• Mol file: 887927-18-6.mol

Synonyms:(R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butyric acid

Chemical Property of (R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butyric acid

There total 5 articles about (R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butyric acid 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: 97.0%

(S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butan-1-ol (887927-17-5) → (R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butyric acid (887927-18-6)

Guidance literature:

With sodium hypochlorite; sodium chlorite; phosphate buffer; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In water; acetonitrile; at 45 ℃; for 4h; pH=7;

DOI:10.1021/ol060457z

Reference yield:

[(S)-1-((2S,6R)-6-Allyl-tetrahydro-pyran-2-ylmethyl)-3-benzyloxy-propoxy]-tert-butyl-diphenyl-silane (887927-14-2) → (R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butyric acid (887927-18-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / K₂OsO₂(OH)4; (DHQD)2PYR; potassium carbonate / K₃Fe(CN)6 / 2-methyl-propan-2-ol; H₂O / 42 h / 4 °C

2: 86 percent / PPTS / dimethylformamide / 2.5 h / 23 - 25 °C

3: 81 percent / hydrogen / Pd(OH)2 / ethyl acetate / 18 h / 23 - 25 °C / 9308.66 Torr

4: 97 percent / phosphate buffer; NaOCl; sodium chlorite / TEMPO / acetonitrile; H₂O / 4 h / 45 °C / pH 7

With sodium hypochlorite; sodium chlorite; phosphate buffer; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI); hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium dihydroxide; potassium hexacyanoferrate(III); In water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ol060457z

Reference yield:

3-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-propane-1,2-diol → (R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butyric acid (887927-18-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / PPTS / dimethylformamide / 2.5 h / 23 - 25 °C

2: 81 percent / hydrogen / Pd(OH)2 / ethyl acetate / 18 h / 23 - 25 °C / 9308.66 Torr

3: 97 percent / phosphate buffer; NaOCl; sodium chlorite / TEMPO / acetonitrile; H₂O / 4 h / 45 °C / pH 7

With sodium hypochlorite; sodium chlorite; phosphate buffer; hydrogen; pyridinium p-toluenesulfonate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium dihydroxide; In water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ol060457z

upstream raw materials:

(S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butan-1-ol

[(S)-1-((2S,6R)-6-Allyl-tetrahydro-pyran-2-ylmethyl)-3-benzyloxy-propoxy]-tert-butyl-diphenyl-silane

{(S)-3-Benzyloxy-1-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-ylmethyl]-propoxy}-tert-butyl-diphenyl-silane

6-[4-benzyloxy-2-(tert-butyldiphenylsilanyloxy)-butyl]-tetrahydropyran-2-one

Downstream raw materials:

C₆₂H₉₆O₁₄Si₂