prop-1-enyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: prop-1-enyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranoside
• CAS No.: 119471-47-5
• Molecular Formula: C₂₅H₂₉ClO₆
• Molecular Weight: 460.955
• Mol file: 119471-47-5.mol

Synonyms:

Chemical Property of prop-1-enyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of prop-1-enyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranoside

There total 1 articles about prop-1-enyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranoside 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:

allyl 3,4-di-O-benzyl-α-L-rhamnosylpyranose (119471-45-3) → prop-1-enyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranoside (119471-47-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaHCO₃ / dimethylformamide / 2 h / Ambient temperature

2: 1,5-cyclo-octadienebisiridium hexafluorophosphate / tetrahydrofuran / 2 h

With sodium hydrogencarbonate; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(88)80077-6

Reference yield:

prop-1-enyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranoside (119471-47-5) → methyl (3R)-3-<(3R)-3-(3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranosyloxy)decanoyloxy>decanoate (119471-55-5)

Guidance literature:

Multi-step reaction with 4 steps

1: HgO, HgCl₂ / H₂O; acetone / 2 h

2: pyridine / 16 h / 25 °C

3: 94 percent / 70 percent HF / pyridine; CH₂Cl₂ / 2 h / 20 °C

4: 83 percent / molecular sieves 4 A / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; 4 A molecular sieve; hydrogen fluoride; mercury dichloride; mercury(II) oxide; boron trifluoride diethyl etherate; In pyridine; dichloromethane; water; acetone;

DOI:10.1016/0008-6215(88)80077-6

Reference yield:

prop-1-enyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranoside (119471-47-5) → methyl (3R)-3-<(3R)-3-<3,4-di-O-benzyl-2-O-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyloxy>decanoyloxy>decanoate (119471-57-7)

Guidance literature:

Multi-step reaction with 5 steps

1: HgO, HgCl₂ / H₂O; acetone / 2 h

2: pyridine / 16 h / 25 °C

3: 94 percent / 70 percent HF / pyridine; CH₂Cl₂ / 2 h / 20 °C

4: 80 percent / molecular sieves 4 A / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 °C

5: 92 percent / 0.375 M hydrazine dithiocarbonate, lutidine / acetic acid / 0.33 h / 20 °C

With pyridine; hydrazine dithiocarbonate; 4 A molecular sieve; lutidine; hydrogen fluoride; mercury dichloride; mercury(II) oxide; boron trifluoride diethyl etherate; In pyridine; dichloromethane; water; acetic acid; acetone;

DOI:10.1016/0008-6215(88)80077-6

upstream raw materials:

allyl 3,4-di-O-benzyl-α-L-rhamnosylpyranose

Downstream raw materials:

3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranosyl fluoride

1-O-acetyl-3,4-di-O-benzyl-2-O-chloroacetyl-L-rhamnopyranose

methyl (3R)-3-<(3R)-3-(3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranosyloxy)decanoyloxy>decanoate

methyl (3R)-3-<(3R)-3-<3,4-di-O-benzyl-2-O-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyloxy>decanoyloxy>decanoate