Benzoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-[8-benzyloxy-14-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-tetradecyloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-[8-benzyloxy-14-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-tetradecyloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 637771-38-1
• Molecular Formula: C₆₀H₇₁NO₁₂
• Molecular Weight: 998.223

Synonyms:Benzoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-[8-benzyloxy-14-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-tetradecyloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-[8-benzyloxy-14-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-tetradecyloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-[8-benzyloxy-14-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-tetradecyloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

There total 10 articles about Benzoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-[8-benzyloxy-14-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-tetradecyloxy]-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: 92.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + Benzoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-(8-benzyloxy-14-carboxy-tetradecyloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (637771-36-9) → Benzoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-[8-benzyloxy-14-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-tetradecyloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (637771-38-1)

Guidance literature:

With dicyclohexyl-carbodiimide; In 1,2-dimethoxyethane; at 20 ℃; for 20h;

DOI:10.1055/s-2003-40337

Reference yield:

1,7-heptandiol (629-30-1) → Benzoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-[8-benzyloxy-14-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-tetradecyloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (637771-38-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 82 percent / imidazole / CH₂Cl₂ / 20 °C

2: 88 percent / Me₂C=CClNMe₂ / CH₂Cl₂ / 0 - 20 °C

3: 61 percent / Mg / tetrahydrofuran / 20 - 80 °C

4: 72 percent / NaH / dimethylformamide / 60 °C

5: 91 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

6: 92 percent / 4 Angstroem molecular sieves / [Rh(III)(MeCN)3(triphos)](TfO)3 / CH₂Cl₂ / 16 h / Heating

7: 90 percent / CAN / acetonitrile; H₂O / 1 h / 20 °C

8: 84 percent / CrO₃; H₂SO₄ / acetone / 2 h / 0 °C

9: 92 percent / DCC / 1,2-dimethoxy-ethane / 20 h / 20 °C

With 1H-imidazole; chromium(VI) oxide; ammonium cerium(IV) nitrate; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; 4 A molecular sieve; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; magnesium; dicyclohexyl-carbodiimide; {Rh(CH₃CN)3(triphos)}(CF₃SO₃)3; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1055/s-2003-40337

Reference yield:

2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside (148926-02-7) → Benzoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-[8-benzyloxy-14-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-tetradecyloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (637771-38-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / 4 Angstroem molecular sieves / [Rh(III)(MeCN)3(triphos)](TfO)3 / CH₂Cl₂ / 16 h / Heating

2: 90 percent / CAN / acetonitrile; H₂O / 1 h / 20 °C

3: 84 percent / CrO₃; H₂SO₄ / acetone / 2 h / 0 °C

4: 92 percent / DCC / 1,2-dimethoxy-ethane / 20 h / 20 °C

With chromium(VI) oxide; ammonium cerium(IV) nitrate; 4 A molecular sieve; sulfuric acid; dicyclohexyl-carbodiimide; {Rh(CH₃CN)3(triphos)}(CF₃SO₃)3; In 1,2-dimethoxyethane; dichloromethane; water; acetone; acetonitrile;

DOI:10.1055/s-2003-40337

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

Benzoic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-(8-benzyloxy-14-carboxy-tetradecyloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

1,7-heptandiol

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

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