Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-((S)-cyano-phenyl-methoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-((S)-cyano-phenyl-methoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 61091-11-0
• Molecular Formula: C₃₄H₄₁NO₁₈
• Molecular Weight: 751.695

Synonyms:

Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-((S)-cyano-phenyl-methoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-((S)-cyano-phenyl-methoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

There total 1 articles about Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-((S)-cyano-phenyl-methoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-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:

acetic anhydride (108-24-7) + (S)-(6-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)(phenyl)acetonitrile (29883-16-7,672-72-0) → Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-((S)-cyano-phenyl-methoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester (61091-11-0)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2004.12.071

Reference yield:

Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-((S)-cyano-phenyl-methoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester (61091-11-0) → 2-bromobenzyl-6-O-(β-D-glucopyranosyl)-β-D-glucopyranoside

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / Pd(OH)2/C / toluene; acetone / 3 h / 25 °C / 750.06 Torr

2: NaH / CH₂Cl₂ / 0.25 h / 25 °C

3: BF₃*Et₂O / CH₂Cl₂ / -50 - 25 °C

4: NaOMe; methanol / 0.17 h / Heating

With methanol; palladium dihydroxide; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In dichloromethane; acetone; toluene;

DOI:10.1016/j.bmcl.2004.12.071

Reference yield:

Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-2-((S)-cyano-phenyl-methoxy)-6-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester (61091-11-0) → benzylalcohol β-D-glucopyranosyl(1→6)-β-D-glucopyranoside (149022-24-2,56775-64-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / Pd(OH)2/C / toluene; acetone / 3 h / 25 °C / 750.06 Torr

2: NaH / CH₂Cl₂ / 0.25 h / 25 °C

3: BF₃*Et₂O / CH₂Cl₂ / -50 - 25 °C

4: NaOMe; methanol / 0.17 h / Heating

With methanol; palladium dihydroxide; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In dichloromethane; acetone; toluene;

DOI:10.1016/j.bmcl.2004.12.071

upstream raw materials:

acetic anhydride

(S)-(6-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)(phenyl)acetonitrile

Downstream raw materials:

benzylalcohol β-D-glucopyranosyl(1→6)-β-D-glucopyranoside

(R)-phenyl-[O²,O³,O⁴-triacetyl-O⁶-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosyloxy]-acetic acid

phenethyl-O-β-D-gluco-pyranosyl-(1′′→6′)-β-D-glucopyranoside

amygdalinic acid

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