(3S^*,4S^*)-1-benzoyloxy-4-benzyloxy-3-methoxymethoxyoctane

Base Information

• Chemical Name: (3S^*,4S^*)-1-benzoyloxy-4-benzyloxy-3-methoxymethoxyoctane
• CAS No.: 136892-21-2
• Molecular Formula: C₂₄H₃₂O₅
• Molecular Weight: 400.515
• Mol file: 136892-21-2.mol

Synonyms:(3S^*,4S^*)-1-benzoyloxy-4-benzyloxy-3-methoxymethoxyoctane

Chemical Property of (3S^*,4S^*)-1-benzoyloxy-4-benzyloxy-3-methoxymethoxyoctane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S^*,4S^*)-1-benzoyloxy-4-benzyloxy-3-methoxymethoxyoctane

There total 6 articles about (3S^*,4S^*)-1-benzoyloxy-4-benzyloxy-3-methoxymethoxyoctane 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: 95.1%

benzoyl chloride (98-88-4) + (3S*,4S*)-4-benzyloxy-3-methoxymethoxyoctan-1-ol (136850-67-4) → (3S*,4S*)-1-benzoyloxy-4-benzyloxy-3-methoxymethoxyoctane (136892-21-2)

Guidance literature:

With pyridine; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1248/cpb.39.1866

Reference yield:

methoxymethyl 5-crotyltetronate → (3S*,4S*)-1-benzoyloxy-4-benzyloxy-3-methoxymethoxyoctane (136892-21-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 75.9 percent / H₂ / 5percent rhodium on alumina / ethyl acetate / 4 h / 5320 Torr

2: 97.7 percent / lithium aluminium hydride / diethyl ether / 2 h / Ambient temperature

3: 78.3 percent / triethylamine / benzene / 6 h / Ambient temperature

4: NaH (60percent oil dispersion) / tetrahydrofuran / 6 h

5: tetrabutylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

6: 95.1 percent / pyridine / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; triethylamine; Rh/Al₂O₃; In tetrahydrofuran; diethyl ether; ethyl acetate; benzene;

DOI:10.1248/cpb.39.1866

Reference yield:

methoxymethyl tetronate (136850-63-0) → (3S*,4S*)-1-benzoyloxy-4-benzyloxy-3-methoxymethoxyoctane (136892-21-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) lithium cyclohexyl isopropylamide / 1) THF, -20 deg C, 2 h, 2) -20 deg C, 3 h

2: 75.9 percent / H₂ / 5percent rhodium on alumina / ethyl acetate / 4 h / 5320 Torr

3: 97.7 percent / lithium aluminium hydride / diethyl ether / 2 h / Ambient temperature

4: 78.3 percent / triethylamine / benzene / 6 h / Ambient temperature

5: NaH (60percent oil dispersion) / tetrahydrofuran / 6 h

6: tetrabutylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

7: 95.1 percent / pyridine / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; lithium cyclohexylisopropylamide; triethylamine; Rh/Al₂O₃; In tetrahydrofuran; diethyl ether; ethyl acetate; benzene;

DOI:10.1248/cpb.39.1866

upstream raw materials:

benzoyl chloride

(3S^*,4S^*)-4-benzyloxy-3-methoxymethoxyoctan-1-ol

(3S^*,4S^*)-1-tert-butyldimethylsilyloxy-4-dihydroxy-3-methoxymethoxyoctane

((3S,4S)-4-Benzyloxy-3-methoxymethoxy-octyloxy)-tert-butyl-dimethyl-silane

Downstream raw materials:

ethyl (5S^*,6S^*)-6-benzyloxy-5-tert-butyldimethylsilyloxy-3-oxodecanoate

(3S^*,4S^*)-1-benzoyloxy-4-benzyloxy-3-tert-butyldimethylsilyloxyoctane

ethyl (5S^*,6S^*)-6-benzyloxy-5-hydroxy-3-oxodecanoate

(3S^*,4S^*)-4-benzyloxy-3-tert-butyldimethylsilyloxyoctanal