2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran

Base Information

• Chemical Name: 2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran
• CAS No.: 632339-32-3
• Molecular Formula: C₃₈H₅₆O₄Si₂
• Molecular Weight: 633.031
• Mol file: 632339-32-3.mol

Synonyms:2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran

Chemical Property of 2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran

There total 10 articles about 2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran 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: 84.0%

2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-ol (632339-31-2) → 2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran (632339-32-3)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - -30 ℃;

DOI:10.1055/s-2003-40856

Reference yield:

(E)-5-(benzyloxy)pent-2-en-1-ol (89923-31-9) → 2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran (632339-32-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 91 percent / D-(-)-diethyl tartrate; Ti(O-iPr)4; t-BuOOH / 4 Angstroem molecular sieves / CH₂Cl₂ / -23 °C

2: 90 percent / Red-Al / diethyl ether / -20 °C

3: 95 percent / PPTS / 25 °C

4: 92 percent / Li; liq. NH₃ / tetrahydrofuran / 25 °C

5: 81 percent / Dess-Martin reagent / CH₂Cl₂ / 25 °C

6: 82 percent / n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / -78 - -5 °C

7: 95 percent / Dowex / methanol; H₂O / Heating

8: 91 percent / imidazole; 4-DMAP / CH₂Cl₂ / 25 °C

9: 25 percent / aq. LiOH; H₂O₂ / tetrahydrofuran

10: TsOH*H₂O / CH₂Cl₂ / 25 °C

11: 90 percent / 2,6-lutidine / dimethylformamide / 25 °C

12: 89 percent / n-BuLi / tetrahydrofuran / -78 °C

13: 84 percent / BF₃*OEt₂; Et₃SiH / CH₂Cl₂ / -78 - -30 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; triethylsilane; tert.-butylhydroperoxide; dmap; lithium hydroxide; n-butyllithium; dowex; diethyl (2S,3S)-tartrate; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; ammonia; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1: Katsuki-Sharpless asymmetric epoxidation / 5: Dess-Martin oxidation;

DOI:10.1055/s-2003-40856

Reference yield:

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol (89956-14-9) → 2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran (632339-32-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 90 percent / Red-Al / diethyl ether / -20 °C

2: 95 percent / PPTS / 25 °C

3: 92 percent / Li; liq. NH₃ / tetrahydrofuran / 25 °C

4: 81 percent / Dess-Martin reagent / CH₂Cl₂ / 25 °C

5: 82 percent / n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / -78 - -5 °C

6: 95 percent / Dowex / methanol; H₂O / Heating

7: 91 percent / imidazole; 4-DMAP / CH₂Cl₂ / 25 °C

8: 25 percent / aq. LiOH; H₂O₂ / tetrahydrofuran

9: TsOH*H₂O / CH₂Cl₂ / 25 °C

10: 90 percent / 2,6-lutidine / dimethylformamide / 25 °C

11: 89 percent / n-BuLi / tetrahydrofuran / -78 °C

12: 84 percent / BF₃*OEt₂; Et₃SiH / CH₂Cl₂ / -78 - -30 °C

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; dmap; lithium hydroxide; n-butyllithium; dowex; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; ammonia; dihydrogen peroxide; pyridinium p-toluenesulfonate; lithium; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 4: Dess-Martin oxidation;

DOI:10.1055/s-2003-40856

upstream raw materials:

2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-ol

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol

(E)-5-(benzyloxy)pent-2-en-1-ol

(S)-5-phenylmethoxypentane-1,3-diol

Downstream raw materials:

4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-carbaldehyde

(Z)-3-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-propenal

(Z)-3-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-prop-2-en-1-ol

(Z)-3-{(2R,3S,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-2-methyl-acrylic acid ethyl ester