Carbamic acid, [(1S)-3-[(2R,3S,4S,5S,6R)-6-[(benzoyloxy)methyl]tetrahydro-5-hydroxy- 3,4-bis(phenylmethoxy)-2H-pyran-2-yl]-1-[(4S,5R)-2-oxo-5-tetradecyl-1, 3-dioxolan-4-yl]propyl](phenylmethyl)-, phenylmethyl ester

Base Information

• Chemical Name: Carbamic acid, [(1S)-3-[(2R,3S,4S,5S,6R)-6-[(benzoyloxy)methyl]tetrahydro-5-hydroxy- 3,4-bis(phenylmethoxy)-2H-pyran-2-yl]-1-[(4S,5R)-2-oxo-5-tetradecyl-1, 3-dioxolan-4-yl]propyl](phenylmethyl)-, phenylmethyl ester
• CAS No.: 634587-27-2
• Molecular Formula: C62H77NO11
• Molecular Weight: 1012.29
• Mol file: 634587-27-2.mol

Synonyms:

Chemical Property of Carbamic acid, [(1S)-3-[(2R,3S,4S,5S,6R)-6-[(benzoyloxy)methyl]tetrahydro-5-hydroxy- 3,4-bis(phenylmethoxy)-2H-pyran-2-yl]-1-[(4S,5R)-2-oxo-5-tetradecyl-1, 3-dioxolan-4-yl]propyl](phenylmethyl)-, phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbamic acid, [(1S)-3-[(2R,3S,4S,5S,6R)-6-[(benzoyloxy)methyl]tetrahydro-5-hydroxy- 3,4-bis(phenylmethoxy)-2H-pyran-2-yl]-1-[(4S,5R)-2-oxo-5-tetradecyl-1, 3-dioxolan-4-yl]propyl](phenylmethyl)-, phenylmethyl ester

There total 34 articles about Carbamic acid, [(1S)-3-[(2R,3S,4S,5S,6R)-6-[(benzoyloxy)methyl]tetrahydro-5-hydroxy- 3,4-bis(phenylmethoxy)-2H-pyran-2-yl]-1-[(4S,5R)-2-oxo-5-tetradecyl-1, 3-dioxolan-4-yl]propyl](phenylmethyl)-, phenylmethyl 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: 76.0%

Benzoic acid (2R,3S,4R,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-diisopropylsilanyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (634587-24-9) → 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) + C62H75NO11

Guidance literature:

Benzoic acid (2R,3S,4R,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-diisopropylsilanyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester; With boron trifluoride diethyl etherate; In dichloromethane; for 5h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; acetic acid; at 20 ℃; for 1h;

Reference yield: 15.0%

Benzoic acid (2R,3S,4R,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-diisopropylsilanyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (634587-24-9) → 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) + Benzoic acid (1S,3R,4S,5S,6R)-1-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2-oxo-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-5,6-bis-benzyloxy-2,7-dioxa-bicyclo[2.2.1]hept-3-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 (863393-17-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃;

DOI:10.1002/anie.200454215

Reference yield:

L-2-[(benzyloxycarbonyl)amino]-4-(tert-butyldimethylsilyloxy)-butylaldehyde (634586-95-1) → 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)

Guidance literature:

Multi-step reaction with 17 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

14: 80 percent / hydrochloric acid / methanol; diethyl ether

15: 83 percent / pyridine / CH₂Cl₂

16: 96 percent / imidazole / dimethylformamide

17: BF₃*Et₂O / CH₂Cl₂ / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; aluminum oxide; potassium hydroxide; chloro-trimethyl-silane; AD-mix-β; C₂F₄Br₂; boron trifluoride diethyl etherate; 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; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2: Sharpless dihydroxylation / 11: Ramberg-Baecklund reaction;

DOI:10.1002/anie.200454215

upstream raw materials:

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

Benzoic acid (2R,3S,4R,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-diisopropylsilanyloxy-6-methoxy-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

Downstream raw materials:

(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

(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