Acetic acid (2R,3S,4R,6S)-4-((2R,4R,5S,6R)-4-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,6S)-4-((2R,4R,5S,6R)-4-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 106023-24-9
• Molecular Formula: C₂₃H₃₄O₈
• Molecular Weight: 438.518
• Mol file: 106023-24-9.mol

Synonyms:Acetic acid (2R,3S,4R,6S)-4-((2R,4R,5S,6R)-4-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3S,4R,6S)-4-((2R,4R,5S,6R)-4-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4R,6S)-4-((2R,4R,5S,6R)-4-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

There total 8 articles about Acetic acid (2R,3S,4R,6S)-4-((2R,4R,5S,6R)-4-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester 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: 61.0%

Methyl-4-O-acetyl-2,6-didesoxy-α-D-lyxo-hexopyranosid (4092-40-4) + (2R,3S,4R)-4-Benzyloxy-3-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran (106023-22-7,106023-23-8) → Acetic acid (2R,3S,4R,6S)-4-((2R,4R,5S,6R)-4-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (106023-24-9)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; at 23 ℃;

DOI:10.1021/jo00004a054

Reference yield:

methyl 4-O-acetyl-3-O-benzyl-2,6-dideoxy-α-D-lyxo-hexopyranoside (4833-12-9) → Acetic acid (2R,3S,4R,6S)-4-((2R,4R,5S,6R)-4-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (106023-24-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / hydrogenation / 10percent Pd/C / ethanol / 760 Torr

2: NBS, 4A molecular sieves(120 mg/mL) / CH₂Cl₂ / 0.75 h / 23 °C

With N-Bromosuccinimide; 4 A molecular sieve; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)84793-0

Reference yield:

(2R,3S,4R)-2,3-O-isopropylidene-6-hepten-2,3,4-triol (106062-13-9) → Acetic acid (2R,3S,4R,6S)-4-((2R,4R,5S,6R)-4-benzyloxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (106023-24-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / NaH / tetrahydrofuran; dimethylformamide / 2 h / Heating

2: 98 percent / 4:1 HOAc-H₂O / 4 h / 100 °C

3: 1.) ozonolysis; 2.) acetyl chloride

4: 84 percent / hydrogenation / 10percent Pd/C / ethanol / 760 Torr

5: NBS, 4A molecular sieves(120 mg/mL) / CH₂Cl₂ / 0.75 h / 23 °C

With N-Bromosuccinimide; 4 A molecular sieve; water; sodium hydride; acetic acid; acetyl chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)84793-0

upstream raw materials:

Methyl-4-O-acetyl-2,6-didesoxy-α-D-lyxo-hexopyranosid

(2R,3S,4R)-4-Benzyloxy-3-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran

methyl 2,6-dideoxy-3-O-benzyl-4-O-methyl-α-D-lyxo-hexopyranoside

methyl 4-O-acetyl-3-O-benzyl-2,6-dideoxy-α-D-lyxo-hexopyranoside