Benzoic acid (2R,3S,4S,5R,6S)-6-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,5R,6S)-6-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 762262-43-1
• Molecular Formula: C₆₅H₈₅NO₁₁
• Molecular Weight: 1056.39
• Mol file: 762262-43-1.mol

Synonyms:Benzoic acid (2R,3S,4S,5R,6S)-6-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Benzoic acid (2R,3S,4S,5R,6S)-6-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4S,5R,6S)-6-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

There total 22 articles about Benzoic acid (2R,3S,4S,5R,6S)-6-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-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: 88.0%

Benzyl-[(S)-3-((2S,3R,4S,5S,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-yl)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester (762262-42-0) + benzoyl chloride (98-88-4) → Benzoic acid (2R,3S,4S,5R,6S)-6-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (762262-43-1)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1002/anie.200454215

Reference yield:

L-2-[(benzyloxycarbonyl)amino]-4-(tert-butyldimethylsilyloxy)-butylaldehyde (634586-95-1) → Benzoic acid (2R,3S,4S,5R,6S)-6-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (762262-43-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 85 percent / tetrahydrofuran

2: AD-mix-β

3: 95 percent / pyridinium p-toluenesulfonate / CH₂Cl₂

4: 86 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran

5: 85 percent / iodine; triphenylphosphine / tetrahydrofuran / Heating

6: triethylamine

7: sodium methoxide / methanol

8: p-toluenesulfonic acid / dimethylformamide; CH₂Cl₂

9: 83 percent / sodium hydride / tetrahydrofuran

10: 93 percent / magnesium monoperoxyphthalate / tetrahydrofuran; H₂O; ethanol / 60 °C

11: 70 percent / C₂F₄Br₂; potassium hydroxide; Al₂O₃ / 2-methyl-propan-2-ol / Heating

12: 66 percent / chlorotrimethylsilane / 0 °C

13: 88 percent / triethylamine / CH₂Cl₂

With aluminum oxide; potassium hydroxide; chloro-trimethyl-silane; AD-mix-β; C₂F₄Br₂; tetrabutyl ammonium fluoride; iodine; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; magnesium monoperoxyphthalate hexahydrate; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2: Sharpless dihydroxylation / 11: Ramberg-Baecklund reaction;

DOI:10.1002/anie.200454215

Reference yield:

[(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-hydroxy-propyl]-carbamic acid benzyl ester (634587-10-3) → Benzoic acid (2R,3S,4S,5R,6S)-6-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (762262-43-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 85 percent / iodine; triphenylphosphine / tetrahydrofuran / Heating

2: triethylamine

3: sodium methoxide / methanol

4: p-toluenesulfonic acid / dimethylformamide; CH₂Cl₂

5: 83 percent / sodium hydride / tetrahydrofuran

6: 93 percent / magnesium monoperoxyphthalate / tetrahydrofuran; H₂O; ethanol / 60 °C

7: 70 percent / C₂F₄Br₂; potassium hydroxide; Al₂O₃ / 2-methyl-propan-2-ol / Heating

8: 66 percent / chlorotrimethylsilane / 0 °C

9: 88 percent / triethylamine / CH₂Cl₂

With aluminum oxide; potassium hydroxide; chloro-trimethyl-silane; C₂F₄Br₂; iodine; sodium methylate; sodium hydride; toluene-4-sulfonic acid; magnesium monoperoxyphthalate hexahydrate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 7: Ramberg-Baecklund reaction;

DOI:10.1002/anie.200454215

upstream raw materials:

Benzyl-[(S)-3-((2S,3R,4S,5S,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-yl)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester

benzoyl chloride

L-2-[(benzyloxycarbonyl)amino]-4-(tert-butyldimethylsilyloxy)-butylaldehyde

[(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-hydroxy-propyl]-carbamic acid benzyl ester

Downstream raw materials:

(3S,4S,5R)-3-Benzylamino-1-((2R,3S,4S,5S,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-nonadecane-4,5-diol

(4S,5S)-3-Benzyl-4-[2-((2R,3S,4S,5S,6R)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-ethyl]-5-((R)-1-hydroxy-pentadecyl)-oxazolidin-2-one

Benzoic acid (2R,3S,4S,5S,6R)-6-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2-oxo-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Benzoic acid (2R,3S,4S,5R,6S)-6-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2-oxo-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester