Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 113842-93-6
• Molecular Formula: C₅₆H₅₉FO₁₁
• Molecular Weight: 927.076
• Mol file: 113842-93-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-3-yloxy)-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:

O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-D-glucopyranose (113842-59-4,113842-91-4) → O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl fluoride (113842-86-7) + Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (113842-93-6)

Guidance literature:

With hexafluoropropene-diethylamine adduct; In diethyl ether; at 20 ℃; for 28h; Yield given. Yields of byproduct given;

DOI:10.1016/0008-6215(87)80136-2

Reference yield:

benzyl bromide (100-39-0) → Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (113842-93-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.)(Bu₃Sn)2O 2.) Bu₄NBr / 1.) toluene, reflux, 4h, 2.) toluene, 80-85 deg C, 24h

2: 100 percent / pyridine / 4 h / 20 °C

3: 93 percent / PdCl₂, AcONa, AcOH / H₂O / 1 h / 70 °C

4: diethyl-1,1,2,3,3,3-hexafluoropropylamine / diethyl ether / 28 h / 20 °C

With pyridine; hexafluoropropene-diethylamine adduct; tetrabutylammomium bromide; sodium acetate; acetic acid; bis(tri-n-butyltin)oxide; palladium dichloride; In diethyl ether; water;

DOI:10.1016/0008-6215(87)80136-2

Reference yield:

allyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-gluco-pyranoside (97777-13-4) → Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (113842-93-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 3.3 g / 0.5M NaOMe / methanol / 2 h / 20 °C

2: 2.3 g / p-TsOH*H₂O / dimethylformamide / 1 h / 20 °C

3: 1.) 50percent NaH in oil / 1.DMF, 20 deg C, 30 min 2.) DMF, 1h

4: 70 percent / AcOH / methanol / 1 h / 80 °C

5: 1.)(Bu₃Sn)2O 2.) Bu₄NBr / 1.) toluene, reflux, 4h, 2.) toluene, 80-85 deg C, 24h

6: 100 percent / pyridine / 4 h / 20 °C

7: 93 percent / PdCl₂, AcONa, AcOH / H₂O / 1 h / 70 °C

8: diethyl-1,1,2,3,3,3-hexafluoropropylamine / diethyl ether / 28 h / 20 °C

With pyridine; hexafluoropropene-diethylamine adduct; tetrabutylammomium bromide; sodium methylate; sodium acetate; sodium hydride; toluene-4-sulfonic acid; acetic acid; bis(tri-n-butyltin)oxide; palladium dichloride; In methanol; diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(87)80136-2

upstream raw materials:

O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-D-glucopyranose

benzyl bromide

allyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-gluco-pyranoside

allyl O-(2,3-di-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside