2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran

Base Information

• Chemical Name: 2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran
• CAS No.: 247146-46-9
• Molecular Formula: C₂₆H₄₈O₄Si₂
• Molecular Weight: 480.836
• Mol file: 247146-46-9.mol

Synonyms:2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran

Chemical Property of 2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-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-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran

There total 14 articles about 2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-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:

t-butyldimethylsiyl triflate (69739-34-0) + (2R,4S,6S)-2-Benzyloxymethyl-6-hydroxymethyl-tetrahydro-pyran-4-ol (215876-11-2) → 2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran (247146-46-9)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃;

DOI:10.1021/ja990860j

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,4S,6S)-2-Benzyloxymethyl-6-hydroxymethyl-tetrahydro-pyran-4-ol (215876-11-2) → 2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran (247146-46-9)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane;

DOI:10.1002/(SICI)1521-3773(19980918)37:17<2354::AID-ANIE2354>3.0.CO;2-9

Reference yield:

tert-butyl (5R)-3-oxo-5-hydroxy-6-benzyloxyhexanoate (147849-63-6) → 2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran (247146-46-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / Me₄NHB(OAc)3; AcOH / acetonitrile / -35 °C

2: CF₃CO₂H / CH₂Cl₂

3: 77 percent / imidazole / CH₂Cl₂ / 0 °C

4: tetrahydrofuran / -78 - -50 °C

5: BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / -20 °C

6: imidazole; DMAP / CH₂Cl₂

With 1H-imidazole; triethylsilane; dmap; boron trifluoride diethyl etherate; acetic acid; trifluoroacetic acid; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; acetonitrile; 1: Reduction / 2: lactonization / 3: silylation / 4: Addition / 5: Reduction / 6: silylation;

DOI:10.1021/ja990860j

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,4S,6S)-2-Benzyloxymethyl-6-hydroxymethyl-tetrahydro-pyran-4-ol

t-butyldimethylsiyl triflate

tert-butyl (5R)-3-oxo-5-hydroxy-6-benzyloxyhexanoate

Downstream raw materials:

[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol

6-{3-[4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-1,1-dimethyl-allyl}-2-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-3,4-dihydro-2H-pyran

trifluoro-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxy)-6-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-ylmethyl ester

C₅₄H₉₂O₁₁SSi₃