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

Base Information

• Chemical Name: (2R,4S,6S)-2-Benzyloxymethyl-6-hydroxymethyl-tetrahydro-pyran-4-ol
• CAS No.: 215876-11-2
• Molecular Formula: C₁₄H₂₀O₄
• Molecular Weight: 252.31
• Mol file: 215876-11-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (2R,4S,6S)-2-Benzyloxymethyl-6-hydroxymethyl-tetrahydro-pyran-4-ol 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:

(2R,4R,6S)-2-Benzyloxymethyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-ol (247146-19-6) → (2R,4S,6S)-2-Benzyloxymethyl-6-hydroxymethyl-tetrahydro-pyran-4-ol (215876-11-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/ja990860j

Reference yield:

(4R,6R)-6-Benzyloxymethyl-2-(4-methoxy-benzyloxymethyl)-4-triethylsilanyloxy-tetrahydro-pyran-2-ol → (2R,4S,6S)-2-Benzyloxymethyl-6-hydroxymethyl-tetrahydro-pyran-4-ol (215876-11-2)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃;

DOI:10.1021/ja990860j

Reference yield:

tert-butyl (5R)-3-oxo-5-hydroxy-6-benzyloxyhexanoate (147849-63-6) → (2R,4S,6S)-2-Benzyloxymethyl-6-hydroxymethyl-tetrahydro-pyran-4-ol (215876-11-2)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/ja990860j

upstream raw materials:

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

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

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

Downstream raw materials:

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

[(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