(R)-1-((tert-butyldiphenylsilyl)oxy)-4-chloro-2-(methoxymethoxy)butane

Base Information

• Chemical Name: (R)-1-((tert-butyldiphenylsilyl)oxy)-4-chloro-2-(methoxymethoxy)butane
• CAS No.: 150943-37-6
• Molecular Formula: C₂₂H₃₁ClO₃Si
• Molecular Weight: 407.025
• Mol file: 150943-37-6.mol

Synonyms:(R)-1-((tert-butyldiphenylsilyl)oxy)-4-chloro-2-(methoxymethoxy)butane

Chemical Property of (R)-1-((tert-butyldiphenylsilyl)oxy)-4-chloro-2-(methoxymethoxy)butane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((tert-butyldiphenylsilyl)oxy)-4-chloro-2-(methoxymethoxy)butane

There total 8 articles about (R)-1-((tert-butyldiphenylsilyl)oxy)-4-chloro-2-(methoxymethoxy)butane 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:

5-O-tert-butyldiphenylsilyl-α,β-L-arabinofuranose (103763-12-8,103763-13-9) → (R)-1-((tert-butyldiphenylsilyl)oxy)-4-chloro-2-(methoxymethoxy)butane (150943-37-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 69 percent / p-toluenesulfonic acid monohydrate / 2 h

2: 67 percent / DMAP / acetonitrile / 18 h / Ambient temperature

3: 95 percent / AIBN, tributyltin hydride / toluene / 6 h / 90 °C

4: 80percent acetic acid / 0.5 h / 90 °C

5: 1.) NaIO₄, 2.) NaBH₄ / 1.) methanol, water, RT, 1.5 h, 2.) 50 min

6: 80 percent / carbon tetrachloride, triphenylphosphine / acetonitrile / 5 h

7: 1.) phosphorus pentaoxide, / 1.) chloroform, RT, 15 min, 2.) chloroform, RT, 24 h

With tetrachloromethane; dmap; phosphorus pentaoxide; sodium tetrahydroborate; sodium periodate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; acetic acid; triphenylphosphine; In toluene; acetonitrile;

DOI:10.1021/jm00035a018

Reference yield:

(3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol (103763-14-0) → (R)-1-((tert-butyldiphenylsilyl)oxy)-4-chloro-2-(methoxymethoxy)butane (150943-37-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 67 percent / DMAP / acetonitrile / 18 h / Ambient temperature

2: 95 percent / AIBN, tributyltin hydride / toluene / 6 h / 90 °C

3: 80percent acetic acid / 0.5 h / 90 °C

4: 1.) NaIO₄, 2.) NaBH₄ / 1.) methanol, water, RT, 1.5 h, 2.) 50 min

5: 80 percent / carbon tetrachloride, triphenylphosphine / acetonitrile / 5 h

6: 1.) phosphorus pentaoxide, / 1.) chloroform, RT, 15 min, 2.) chloroform, RT, 24 h

With tetrachloromethane; dmap; phosphorus pentaoxide; sodium tetrahydroborate; sodium periodate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; acetic acid; triphenylphosphine; In toluene; acetonitrile;

DOI:10.1021/jm00035a018

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (R)-1-((tert-butyldiphenylsilyl)oxy)-4-chloro-2-(methoxymethoxy)butane (150943-37-6)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole / dimethylformamide

2: 69 percent / p-toluenesulfonic acid monohydrate / 2 h

3: 67 percent / DMAP / acetonitrile / 18 h / Ambient temperature

4: 95 percent / AIBN, tributyltin hydride / toluene / 6 h / 90 °C

5: 80percent acetic acid / 0.5 h / 90 °C

6: 1.) NaIO₄, 2.) NaBH₄ / 1.) methanol, water, RT, 1.5 h, 2.) 50 min

7: 80 percent / carbon tetrachloride, triphenylphosphine / acetonitrile / 5 h

8: 1.) phosphorus pentaoxide, / 1.) chloroform, RT, 15 min, 2.) chloroform, RT, 24 h

With 1H-imidazole; tetrachloromethane; dmap; phosphorus pentaoxide; sodium tetrahydroborate; sodium periodate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; acetic acid; triphenylphosphine; In N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jm00035a018

upstream raw materials:

Dimethoxymethane

(R)-1-O-(tert-butyldiphenylsilyl)-4-chloro-1,2-butanediol

5-O-tert-butyldiphenylsilyl-α,β-L-arabinofuranose

(3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

Downstream raw materials:

9-[((3R)-1-hydroxymethyl-3-phosphono)propyloxymethyl]guanine

(R)-diethyl <3-((2-acetamido-1,6-dihydro-6-oxo-7H-purin-7-yl)methoxy)-4-(benzoyloxy)butyl>phosphonate

(R)-2-((2-acetamido-1,6-dihydro-6-oxo-7H-purin-7-yl)methoxy)-4-chlorobutyl benzoate

(R)-4-chloro-2-(methoxymethoxy)butyl benzoate