(2R,3R,4S,6R)-2-Benzyloxymethyl-6-(2-hydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-ol

Base Information

• Chemical Name: (2R,3R,4S,6R)-2-Benzyloxymethyl-6-(2-hydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-ol
• CAS No.: 884338-28-7
• Molecular Formula: C₁₆H₂₄O₄
• Molecular Weight: 280.364
• Mol file: 884338-28-7.mol

Synonyms:(2R,3R,4S,6R)-2-Benzyloxymethyl-6-(2-hydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-ol

Chemical Property of (2R,3R,4S,6R)-2-Benzyloxymethyl-6-(2-hydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,6R)-2-Benzyloxymethyl-6-(2-hydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-ol

There total 8 articles about (2R,3R,4S,6R)-2-Benzyloxymethyl-6-(2-hydroxy-ethyl)-3-methyl-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: 89.0%

C40H56O8Si (1035662-48-6) → (2R,3R,4S,6R)-2-Benzyloxymethyl-6-(2-hydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-ol (884338-28-7)

Guidance literature:

With pyridine hydrogenfluoride; at 25 ℃; for 6h;

DOI:10.1016/j.tet.2008.03.039

Reference yield:

Methanesulfonic acid (S)-1-((4S,5R,6R)-6-benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-ylmethyl)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester → (2R,3R,4S,6R)-2-Benzyloxymethyl-6-(2-hydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-ol (884338-28-7)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; at 20 ℃; for 48h;

DOI:10.1016/j.tetlet.2006.01.130

Reference yield:

((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-acetaldehyde → (2R,3R,4S,6R)-2-Benzyloxymethyl-6-(2-hydroxy-ethyl)-3-methyl-tetrahydro-pyran-4-ol (884338-28-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: CH₂Cl₂ / 4 h / 20 °C

2.1: DIBAL-H / CH₂Cl₂ / 0.33 h / -78 °C

3.1: D-(-)-DIPT; Ti(O-iPr)4; TBHP / CH₂Cl₂ / 3 h / -20 °C

3.2: 92 percent / Red-Al / tetrahydrofuran / 3 h / -10 °C

4.1: Et₃N; DMAP / dimethylformamide / 5 h / 0 - 20 °C

5.1: Et₃N; DMAP / CH₂Cl₂ / 0.5 h / 0 - 20 °C

6.1: CSA / methanol / 48 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; camphor-10-sulfonic acid; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Sharpless epoxidation;

DOI:10.1016/j.tetlet.2006.01.130

upstream raw materials:

(E)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-but-2-en-1-ol

(S)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butane-1,3-diol

C₄₀H₅₆O₈Si

Downstream raw materials:

2-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-ethanol

(S)-1-[(2R,4S,5S,6R)-6-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-5-methyl-tetrahydro-pyran-2-yl]-pent-3-yn-2-ol

{(2S,3S,4S,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[(S)-2-hydroxy-2-((1S,2S)-2-methyl-cyclopropyl)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid allyl ester

(2R,3S,4S,6R)-2-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-6-[(S)-2-((1S,2S)-2-methyl-cyclopropyl)-2-triethylsilanyloxy-ethyl]-tetrahydro-pyran