{(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

Base Information

• Chemical Name: {(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
• CAS No.: 887927-16-4
• Molecular Formula: C₃₈H₅₂O₅Si
• Molecular Weight: 616.913
• Mol file: 887927-16-4.mol

Synonyms:{(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

Chemical Property of {(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(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

There total 3 articles about {(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 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%

3-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-propane-1,2-diol + 2,2-dimethoxy-propane (77-76-9) → {(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 (887927-16-4) + {(S)-3-Benzyloxy-1-[(2S,6R)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-ylmethyl]-propoxy}-tert-butyl-diphenyl-silane

Guidance literature:

With pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide; at 23 - 25 ℃; for 2.5h;

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) → {(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 (887927-16-4)

Guidance literature:

Multi-step reaction with 2 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

With hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI); pyridinium p-toluenesulfonate; potassium carbonate; potassium hexacyanoferrate(III); In water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ol060457z

Reference yield:

6-[4-benzyloxy-2-(tert-butyldiphenylsilanyloxy)-butyl]-tetrahydropyran-2-one (500208-43-5) → {(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 (887927-16-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

1.2: 51 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 1.5 h / -30 °C

2.1: 94 percent / K₂OsO₂(OH)4; (DHQD)2PYR; potassium carbonate / K₃Fe(CN)6 / 2-methyl-propan-2-ol; H₂O / 42 h / 4 °C

3.1: 86 percent / PPTS / dimethylformamide / 2.5 h / 23 - 25 °C

With hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI); pyridinium p-toluenesulfonate; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ol060457z

upstream raw materials:

2,2-dimethoxy-propane

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

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

Downstream 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

(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

C₆₂H₉₆O₁₄Si₂