1,2,3,4-tetra-O-acetyl-6,7-O-isopropylidene-8-O-benzyl-L-threo-D-talo-octopyranose

Base Information

• Chemical Name: 1,2,3,4-tetra-O-acetyl-6,7-O-isopropylidene-8-O-benzyl-L-threo-D-talo-octopyranose
• CAS No.: 138584-54-0
• Molecular Formula: C₂₆H₃₄O₁₂
• Molecular Weight: 538.549
• Mol file: 138584-54-0.mol

Synonyms:

Chemical Property of 1,2,3,4-tetra-O-acetyl-6,7-O-isopropylidene-8-O-benzyl-L-threo-D-talo-octopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2,3,4-tetra-O-acetyl-6,7-O-isopropylidene-8-O-benzyl-L-threo-D-talo-octopyranose

There total 6 articles about 1,2,3,4-tetra-O-acetyl-6,7-O-isopropylidene-8-O-benzyl-L-threo-D-talo-octopyranose 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:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) → 1,2,3,4-tetra-O-acetyl-6,7-O-isopropylidene-8-O-benzyl-L-threo-D-talo-octopyranose (138584-54-0)

Guidance literature:

Multi-step reaction with 6 steps

1: BF₃*Et₂O / CH₂Cl₂ / 5 h / -85 °C

2: pyridine / 4 h / 25 °C

3: 50 percent / dicyclohexano-18-crown-6, KMnO₄ / CH₂Cl₂ / 6 h / Ambient temperature

4: 2.35 g / pyridine / 5 h / Ambient temperature

5: 1) DIBALH, 2) citric acid / 1) CH₂Cl₂, -90 deg C, 4 h, 2) MeOH, rt

6: pyridine, DMAP / 12 h / Ambient temperature

With pyridine; dmap; perhydrodibenzo-18-crown-6; potassium permanganate; boron trifluoride diethyl etherate; diisobutylaluminium hydride; citric acid; In dichloromethane;

DOI:10.1016/S0040-4020(01)81954-2

Reference yield:

(1'S,4''R,5R,5''S)-5-[(5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)hydromethyl]-5H-furan-2-one (345341-14-2) → 1,2,3,4-tetra-O-acetyl-6,7-O-isopropylidene-8-O-benzyl-L-threo-D-talo-octopyranose (138584-54-0)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 4 h / 25 °C

2: 50 percent / dicyclohexano-18-crown-6, KMnO₄ / CH₂Cl₂ / 6 h / Ambient temperature

3: 2.35 g / pyridine / 5 h / Ambient temperature

4: 1) DIBALH, 2) citric acid / 1) CH₂Cl₂, -90 deg C, 4 h, 2) MeOH, rt

5: pyridine, DMAP / 12 h / Ambient temperature

With pyridine; dmap; perhydrodibenzo-18-crown-6; potassium permanganate; diisobutylaluminium hydride; citric acid; In dichloromethane;

DOI:10.1016/S0040-4020(01)81954-2

Reference yield:

5-O-(trimethylsilyl)-6,7-O-isopropylidene-8-O-benzyl-2,3-dideoxy-L-galacto-oct-2-enono-1,4-lactone (138584-51-7) → 1,2,3,4-tetra-O-acetyl-6,7-O-isopropylidene-8-O-benzyl-L-threo-D-talo-octopyranose (138584-54-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 50 percent / dicyclohexano-18-crown-6, KMnO₄ / CH₂Cl₂ / 6 h / Ambient temperature

2: 2.35 g / pyridine / 5 h / Ambient temperature

3: 1) DIBALH, 2) citric acid / 1) CH₂Cl₂, -90 deg C, 4 h, 2) MeOH, rt

4: pyridine, DMAP / 12 h / Ambient temperature

With pyridine; dmap; perhydrodibenzo-18-crown-6; potassium permanganate; diisobutylaluminium hydride; citric acid; In dichloromethane;

DOI:10.1016/S0040-4020(01)81954-2

upstream raw materials:

acetic anhydride

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

(1'S,4''R,5R,5''S)-5-[(5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)hydromethyl]-5H-furan-2-one

5-O-(trimethylsilyl)-6,7-O-isopropylidene-8-O-benzyl-2,3-dideoxy-L-galacto-oct-2-enono-1,4-lactone