Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 90302-53-7
• Molecular Formula: C₃₁H₃₃F₃O₈S
• Molecular Weight: 622.659
• Mol file: 90302-53-7.mol

Synonyms:Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property of Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

There total 6 articles about Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-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:

trifluoromethylsulfonic anhydride (358-23-6) + allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside (83921-79-3) → Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (90302-53-7)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1081/CAR-100108658

Reference yield:

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3) → Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (90302-53-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 43.15 g / TBAB; 2,4,6-trimethylpyridine / 16 h / 45 °C

2.1: NaOMe / methanol / 1.5 h

3.1: 46.53 g / NaH / dimethylformamide / 20 h / 23 °C

4.1: TMSOTf / 0.33 h / 0 °C

4.2: 85 percent / MeONa / methanol / 20 h / 23 °C

5.1: pyridine / CH₂Cl₂ / 1.5 h / 0 °C

With pyridine; 2,4,6-trimethyl-pyridine; trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Zemplen deacetylation;

DOI:10.1081/CAR-100108658

Reference yield:

D-glucose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → Trifluoro-methanesulfonic acid (2R,3R,4S,5R,6R)-2-allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (90302-53-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: HBr; AcOH / CH₂Cl₂ / 1.5 h / 0 - 23 °C

2.1: 43.15 g / TBAB; 2,4,6-trimethylpyridine / 16 h / 45 °C

3.1: NaOMe / methanol / 1.5 h

4.1: 46.53 g / NaH / dimethylformamide / 20 h / 23 °C

5.1: TMSOTf / 0.33 h / 0 °C

5.2: 85 percent / MeONa / methanol / 20 h / 23 °C

6.1: pyridine / CH₂Cl₂ / 1.5 h / 0 °C

With pyridine; 2,4,6-trimethyl-pyridine; trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; hydrogen bromide; sodium methylate; sodium hydride; acetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Zemplen deacetylation;

DOI:10.1081/CAR-100108658

upstream raw materials:

trifluoromethylsulfonic anhydride

allyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

D-glucose pentaacetate

Downstream raw materials:

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-mannopyranose

allyl (2-azido-3,4,6-tri-O-benzyl-2-deoxy)-β-D-mannopyranoside