Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R)-2,4-bis-benzyloxy-5-((R)-1,2-bis-benzyloxy-ethyl)-tetrahydro-furan-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R)-2,4-bis-benzyloxy-5-((R)-1,2-bis-benzyloxy-ethyl)-tetrahydro-furan-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 144261-03-0
• Molecular Formula: C₆₃H₆₆O₁₂
• Molecular Weight: 1015.21
• Mol file: 144261-03-0.mol

Synonyms:Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R)-2,4-bis-benzyloxy-5-((R)-1,2-bis-benzyloxy-ethyl)-tetrahydro-furan-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R)-2,4-bis-benzyloxy-5-((R)-1,2-bis-benzyloxy-ethyl)-tetrahydro-furan-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R)-2,4-bis-benzyloxy-5-((R)-1,2-bis-benzyloxy-ethyl)-tetrahydro-furan-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester

There total 5 articles about Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R)-2,4-bis-benzyloxy-5-((R)-1,2-bis-benzyloxy-ethyl)-tetrahydro-furan-3-yloxy]-tetrahydro-pyran-2-ylmethyl 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:

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose (4356-77-8,35094-65-6,61277-56-3,65556-30-1,78185-13-4,78185-15-6,109958-31-8,109958-33-0,113532-02-8,59433-13-5) → Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R)-2,4-bis-benzyloxy-5-((R)-1,2-bis-benzyloxy-ethyl)-tetrahydro-furan-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester (144261-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1: TiBr₄ / CH₂Cl₂; ethyl acetate / 1.25 h / Ambient temperature

2: 1) Hg(CN)2, molecular sieves (4 Angstroem) / 1) nitromethane, toluene, 1 h, 2) toluene, r. t., 20 h

With 4 A molecular sieve; mercury(II) cyanide; titanium(IV) bromide; In dichloromethane; ethyl acetate;

DOI:10.1016/S0008-6215(00)90992-3

Reference yield:

1,2-Di-O-acetyl-3,5,6-tri-O-benzyl-α,β-D-glucofuranose (51515-91-4) → Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R)-2,4-bis-benzyloxy-5-((R)-1,2-bis-benzyloxy-ethyl)-tetrahydro-furan-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester (144261-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) molecular sieves (4 Angstroem), 2) trimethylsilyl triflate / 1) CH₂Cl₂, r. t., 1 h, 2) r. t., 2 h

2: 91 percent / NaOCH₃ / CHCl₃; methanol

3: 1) Hg(CN)2, molecular sieves (4 Angstroem) / 1) nitromethane, toluene, 1 h, 2) toluene, r. t., 20 h

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; mercury(II) cyanide; In methanol; chloroform;

DOI:10.1016/S0008-6215(00)90992-3

Reference yield:

benzyl 2-O-acetyl-3,5,6-tri-O-benzyl-β-D-glucofuranoside (96711-58-9,144301-89-3) → Acetic acid (2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R)-2,4-bis-benzyloxy-5-((R)-1,2-bis-benzyloxy-ethyl)-tetrahydro-furan-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester (144261-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / NaOCH₃ / CHCl₃; methanol

2: 1) Hg(CN)2, molecular sieves (4 Angstroem) / 1) nitromethane, toluene, 1 h, 2) toluene, r. t., 20 h

With 4 A molecular sieve; sodium methylate; mercury(II) cyanide; In methanol; chloroform;

DOI:10.1016/S0008-6215(00)90992-3

upstream raw materials:

6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl bromide

benzyl 3,5,6-tri-O-benzyl-β-D-glucofuranoside

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose

1,2-Di-O-acetyl-3,5,6-tri-O-benzyl-α,β-D-glucofuranose

Downstream raw materials:

benzyl 3,5,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-β-D-glucofuranoside