[(1S,2R)-2-Benzyloxy-1-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-propoxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(1S,2R)-2-Benzyloxy-1-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-propoxy]-tert-butyl-dimethyl-silane
• CAS No.: 169392-07-8
• Molecular Formula: C₂₄H₄₂O₄Si
• Molecular Weight: 422.681
• Mol file: 169392-07-8.mol

Synonyms:

Chemical Property of [(1S,2R)-2-Benzyloxy-1-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-propoxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,2R)-2-Benzyloxy-1-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-propoxy]-tert-butyl-dimethyl-silane

There total 13 articles about [(1S,2R)-2-Benzyloxy-1-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-propoxy]-tert-butyl-dimethyl-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:

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3R)-3-Benzyloxy-1-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-butan-2-ol → [(1S,2R)-2-Benzyloxy-1-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-propoxy]-tert-butyl-dimethyl-silane (169392-07-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; Yield given;

DOI:10.1246/cl.1995.881

Reference yield:

(R)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol (58475-17-5) → [(1S,2R)-2-Benzyloxy-1-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-propoxy]-tert-butyl-dimethyl-silane (169392-07-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 82 percent / NaH, Bu₄NI / tetrahydrofuran / Ambient temperature

2: 2 M aq. HCl

3: tetrahydrofuran / Ambient temperature

4: 94 percent / TsOH / CH₂Cl₂ / 0 °C

5: 98 percent / MeI, NaHCO₃ / H₂O; tetrahydrofuran

6: 78 percent / tetrahydrofuran / -78 °C

7: 94 percent / Swern reagent

8: 99 percent / tetrahydrofuran / -78 °C

9: TsOH / Ambient temperature

10: imidazole / dimethylformamide / 0 °C

With 1H-imidazole; hydrogenchloride; swern reagent; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; methyl iodide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1246/cl.1995.881

Reference yield:

[(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d] [1,3]dioxol-5-yl]-2-hydroxy-ethyl]4-methylbenzenesulfonate (58475-16-4) → [(1S,2R)-2-Benzyloxy-1-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-propoxy]-tert-butyl-dimethyl-silane (169392-07-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 90 percent / LiAlH₄ / tetrahydrofuran

2: 82 percent / NaH, Bu₄NI / tetrahydrofuran / Ambient temperature

3: 2 M aq. HCl

4: tetrahydrofuran / Ambient temperature

5: 94 percent / TsOH / CH₂Cl₂ / 0 °C

6: 98 percent / MeI, NaHCO₃ / H₂O; tetrahydrofuran

7: 78 percent / tetrahydrofuran / -78 °C

8: 94 percent / Swern reagent

9: 99 percent / tetrahydrofuran / -78 °C

10: TsOH / Ambient temperature

11: imidazole / dimethylformamide / 0 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; swern reagent; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; methyl iodide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1246/cl.1995.881

upstream raw materials:

tert-butyldimethylsilyl chloride

(R)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol

[(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d] [1,3]dioxol-5-yl]-2-hydroxy-ethyl]4-methylbenzenesulfonate

3-deoxy-1,2-O-isopropylidene-D-glucose