2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: 2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 365441-30-1
• Molecular Formula: C₇₄H₁₁₀O₁₀Si₃
• Molecular Weight: 1243.94
• Mol file: 365441-30-1.mol

Synonyms:2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of 2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester

There total 21 articles about 2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl 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:

1 ,5-pentanediol (111-29-5) → 2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester (365441-30-1)

Guidance literature:

Multi-step reaction with 14 steps

1: 96 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: PCC; molecular sieves 4 Angstroem powder / CH₂Cl₂ / 1.5 h / 20 °C

3: n-BuLi; t-BuOK; (-)-Ipc₂BOMe / BF₃*OEt₂ / tetrahydrofuran / -78 °C

4: 93 percent / NaH / dimethylformamide / 3 h / 20 °C

5: 94 percent / OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 48 h / 20 °C

6: 96 percent / Pb(OAc)4 / benzene / 0.5 h / 20 °C

7: 64 percent / Sn / tetrahydrofuran; ethanol; H₂O / 4 h / 20 °C / sonication

8: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

9: 98 percent / TBAF / tetrahydrofuran / 2 h / 60 °C

10: 96 percent / DMAP / CH₂Cl₂ / 1 h / 0 °C

11: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

12: 89 percent / HCO₂H / diethyl ether / 0.17 h / 0 °C

13: 94 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; dmap; tin; osmium(VIII) oxide; n-butyllithium; formic acid; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; (-)-B-methoxydiisopinocampheylborane; pyridinium chlorochromate; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene; 3: Brown crotylboration;

DOI:10.1016/S0040-4039(01)01069-3

Reference yield:

5-[(triphenylmethyl)oxy]pentanol (147726-64-5) → 2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester (365441-30-1)

Guidance literature:

Multi-step reaction with 13 steps

1: PCC; molecular sieves 4 Angstroem powder / CH₂Cl₂ / 1.5 h / 20 °C

2: n-BuLi; t-BuOK; (-)-Ipc₂BOMe / BF₃*OEt₂ / tetrahydrofuran / -78 °C

3: 93 percent / NaH / dimethylformamide / 3 h / 20 °C

4: 94 percent / OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 48 h / 20 °C

5: 96 percent / Pb(OAc)4 / benzene / 0.5 h / 20 °C

6: 64 percent / Sn / tetrahydrofuran; ethanol; H₂O / 4 h / 20 °C / sonication

7: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

8: 98 percent / TBAF / tetrahydrofuran / 2 h / 60 °C

9: 96 percent / DMAP / CH₂Cl₂ / 1 h / 0 °C

10: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

11: 89 percent / HCO₂H / diethyl ether / 0.17 h / 0 °C

12: 94 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; dmap; tin; osmium(VIII) oxide; n-butyllithium; formic acid; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; 4-methylmorpholine N-oxide; (-)-B-methoxydiisopinocampheylborane; pyridinium chlorochromate; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene; 2: Brown crotylboration;

DOI:10.1016/S0040-4039(01)01069-3

Reference yield:

5-triphenylmethoxypentanal (258331-72-5) → 2,2-dimethyl-propionic acid 3,4-bis-benzyloxy-6-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-octyl]-allyl}-5-methyl-tetrahydro-pyran-2-ylmethyl ester (365441-30-1)

Guidance literature:

Multi-step reaction with 12 steps

1: n-BuLi; t-BuOK; (-)-Ipc₂BOMe / BF₃*OEt₂ / tetrahydrofuran / -78 °C

2: 93 percent / NaH / dimethylformamide / 3 h / 20 °C

3: 94 percent / OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 48 h / 20 °C

4: 96 percent / Pb(OAc)4 / benzene / 0.5 h / 20 °C

5: 64 percent / Sn / tetrahydrofuran; ethanol; H₂O / 4 h / 20 °C / sonication

6: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7: 98 percent / TBAF / tetrahydrofuran / 2 h / 60 °C

8: 96 percent / DMAP / CH₂Cl₂ / 1 h / 0 °C

9: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

10: 89 percent / HCO₂H / diethyl ether / 0.17 h / 0 °C

11: 94 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; dmap; tin; osmium(VIII) oxide; n-butyllithium; formic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; 4-methylmorpholine N-oxide; (-)-B-methoxydiisopinocampheylborane; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene; 1: Brown crotylboration;

DOI:10.1016/S0040-4039(01)01069-3

upstream raw materials:

1 ,5-pentanediol

benzyl bromide

4-O-benzyl-2-methyl-1,6-anhydro-β-D-glucopyranose

5-[(triphenylmethyl)oxy]pentanol