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

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 176380-05-5
• Molecular Formula: C₃₄H₄₂O₁₄
• Molecular Weight: 674.699
• Mol file: 176380-05-5.mol

Synonyms:

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

There total 2 articles about Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methoxy-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: 42.0%

Methyl 2,3-di-O-benzyl-β-D-xylopyranoside (80973-59-7) + β-D-galactose peracetate (4163-60-4) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (176380-05-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane;

DOI:10.1560/LXUM-GKYP-R6RF-08TF

Reference yield:

methyl 2,3-di-O-benzyl-4-O-trityl-β-D-xylopyranoside (96016-71-6) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (176380-05-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / aq. TFA / CHCl₃ / 0.5 h / 20 °C

2: 42 percent / molecular sieves 4A; trimethylsilyl triflate / CH₂Cl₂

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; trifluoroacetic acid; In dichloromethane; chloroform;

DOI:10.1560/LXUM-GKYP-R6RF-08TF

Reference yield:

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (176380-05-5) → C46H48O18

Guidance literature:

Multi-step reaction with 6 steps

1.1: MeONa; MeOH

2.1: TsOH*H₂O / acetonitrile

3.1: Et₃N / acetonitrile / 3 h

4.1: Hg(CN)2; HgBr₂; molecular sieves 4A / acetonitrile

4.2: acetonitrile

5.1: 7 mg / aq. TFA / CHCl₃ / 0.5 h / 20 °C

6.1: H₂ / 10 percent Pd/C / ethanol; acetic acid

With methanol; 4 A molecular sieve; hydrogen; sodium methylate; mercury(II) cyanide; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; mercury dibromide; palladium on activated charcoal; In ethanol; chloroform; acetic acid; acetonitrile;

DOI:10.1560/LXUM-GKYP-R6RF-08TF

upstream raw materials:

Methyl 2,3-di-O-benzyl-β-D-xylopyranoside

β-D-galactose peracetate

methyl 2,3-di-O-benzyl-4-O-trityl-β-D-xylopyranoside

Downstream raw materials:

Benzoic acid (4aR,6R,7R,8R,8aS)-6-((3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

methyl O-(2,3,4-tri-O-benzoyl-α-L-fucopyranosyl)-(1->2)-O-(3-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzyl-β-D-xylopyranoside

methyl O-(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl)-(1->2)-O-(3-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-benzyl-β-D-xylopyranoside