(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

Base Information

• Chemical Name: (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
• CAS No.: 634587-28-3
• Molecular Formula: C₄₇H₆₇NO₈
• Molecular Weight: 774.051
• Mol file: 634587-28-3.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 28 articles about (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 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: 96.0%

C55H73NO10 → (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 (634587-28-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 90 ℃; Heating / reflux;

Reference yield:

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 (634587-27-2) → (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 (634587-28-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; Heating;

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) → (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 (634587-28-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / triethylamine / CH₂Cl₂

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

3: 83 percent / pyridine / CH₂Cl₂

4: 96 percent / imidazole / dimethylformamide

5: BF₃*Et₂O / CH₂Cl₂ / 0 °C

6: sodium hydroxide / H₂O; dioxane / Heating

With pyridine; 1H-imidazole; hydrogenchloride; sodium hydroxide; boron trifluoride diethyl etherate; triethylamine; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/anie.200454215

upstream raw materials:

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

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

[(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-iodo-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