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

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-methoxy-benzyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 210347-88-9
• Molecular Formula: C₃₄H₄₄O₁₉
• Molecular Weight: 756.712
• Mol file: 210347-88-9.mol

Synonyms:Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-methoxy-benzyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

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

There total 1 articles about Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-methoxy-benzyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-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: 70.0%

4-Methoxybenzyl alcohol (105-13-5) + 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide (4753-07-5) → Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-methoxy-benzyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (210347-88-9)

Guidance literature:

With mercury(II) diacetate; for 2h;

DOI:10.1016/S0008-6215(97)10043-X

Reference yield: 95.0%

Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-methoxy-benzyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (210347-88-9) → (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (210347-89-0)

Guidance literature:

With triethylamine; In methanol; water; Ambient temperature;

DOI:10.1016/S0008-6215(97)10043-X

Reference yield:

Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-methoxy-benzyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (210347-88-9) → 4-methoxybenzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-O-2,3,6-tri-O-benzyl-β-D-glucopyranoside (210347-94-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / Et₃N / methanol; H₂O / Ambient temperature

2: 1.) p-TsOH*H₂O / 1.) 70 deg C, 2 h, 2.) MeOH, H₂O, reflux, 3 h

3: 94 percent / NaH / dimethylformamide / 3 h / 0 °C

4: 87 percent / 70percent acetic acid / 3 h / Heating

5: 1.) p-TsOH*H₂O, 2.) 80percent AcOH / 1.) toluene, room temperature, 1.5 h, 2.) H₂O, room temperature, 1.5 h

6: 77 percent / trimethylsilyl trifluoromethane sulfonate / CH₂Cl₂ / 0.5 h / -70 °C

With trimethylsilyl trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)10043-X

upstream raw materials:

4-Methoxybenzyl alcohol

2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide

Downstream raw materials:

(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

4-methoxybenzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-O-2,3,6-tri-O-benzyl-β-D-glucopyranoside

(2R,3R,4R,5S,6R)-5-((3aS,4R,6S,7R,7aR)-7-Hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-hydroxymethyl-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3,4-diol

(2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-[(2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3,4-diol