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

Base Information

• Chemical Name: 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
• CAS No.: 119471-57-7
• Molecular Formula: C₆₁H₈₄O₁₃
• Molecular Weight: 1025.33
• Mol file: 119471-57-7.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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: 92.0%

methyl (3R)-3-<(3R)-3-<3,4-di-O-benzyl-2-O-(3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyloxy>decanoyloxy>decanoate (119501-95-0) → 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:

With hydrazine dithiocarbonate; lutidine; In acetic acid; at 20 ℃; for 0.333333h;

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

Reference yield:

allyl 3,4-di-O-benzyl-α-L-rhamnosylpyranose (119471-45-3) → 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 7 steps

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

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

3: HgO, HgCl₂ / H₂O; acetone / 2 h

4: pyridine / 16 h / 25 °C

5: 94 percent / 70 percent HF / pyridine; CH₂Cl₂ / 2 h / 20 °C

6: 80 percent / molecular sieves 4 A / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 °C

7: 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; sodium hydrogencarbonate; mercury dichloride; mercury(II) oxide; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; boron trifluoride diethyl etherate; In tetrahydrofuran; pyridine; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;

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

Reference yield:

3,4-di-O-benzyl-2-O-chloroacetyl-α/β-L-rhamnopyranose → 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 4 steps

1: pyridine / 16 h / 25 °C

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

3: 80 percent / molecular sieves 4 A / BF₃*Et₂O / CH₂Cl₂ / 0.25 h / 20 °C

4: 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; boron trifluoride diethyl etherate; In pyridine; dichloromethane; acetic acid;

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

upstream raw materials:

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

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

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

allyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranoside