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

Base Information

• Chemical Name: 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
• CAS No.: 634587-25-0
• Molecular Formula: C₆₃H₇₉NO₁₂
• Molecular Weight: 1042.32
• Mol file: 634587-25-0.mol

Synonyms: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

Chemical Property of 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

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-oxo-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

There total 25 articles about 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 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: 83.0%

Benzoic acid (2R,3S,4S,5R,6S)-6-[(3S,4S,5R)-3-(benzyl-benzyloxycarbonyl-amino)-4,5-dihydroxy-nonadecyl]-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (634587-23-8) + bis(trichloromethyl) carbonate (32315-10-9) → 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 (634587-25-0)

Guidance literature:

With pyridine; In dichloromethane;

DOI:10.1002/anie.200454215

Reference yield:

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) → 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 (634587-25-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / hydrochloric acid / methanol; diethyl ether

2: 83 percent / pyridine / CH₂Cl₂

With pyridine; hydrogenchloride; In methanol; diethyl ether; dichloromethane;

DOI:10.1002/anie.200454215

Reference yield:

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) → 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 (634587-25-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / triethylamine / CH₂Cl₂

2: 80 percent / hydrochloric acid / methanol; diethyl ether

3: 83 percent / pyridine / CH₂Cl₂

With pyridine; hydrogenchloride; triethylamine; In methanol; diethyl ether; dichloromethane;

DOI:10.1002/anie.200454215

upstream raw materials:

Benzoic acid (2R,3S,4S,5R,6S)-6-[(3S,4S,5R)-3-(benzyl-benzyloxycarbonyl-amino)-4,5-dihydroxy-nonadecyl]-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

bis(trichloromethyl) carbonate

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,4R,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-(fluoro-diisopropyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester