Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(S)-3-benzyloxycarbonylamino-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propylsulfanyl]-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(S)-3-benzyloxycarbonylamino-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propylsulfanyl]-tetrahydro-pyran-4-yl ester
• CAS No.: 634587-17-0
• Molecular Formula: C₄₄H₆₉NO₁₃S
• Molecular Weight: 852.097

Synonyms:Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(S)-3-benzyloxycarbonylamino-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propylsulfanyl]-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(S)-3-benzyloxycarbonylamino-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propylsulfanyl]-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(S)-3-benzyloxycarbonylamino-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propylsulfanyl]-tetrahydro-pyran-4-yl ester

There total 15 articles about Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(S)-3-benzyloxycarbonylamino-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propylsulfanyl]-tetrahydro-pyran-4-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: 90.0%

[(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-iodo-propyl]-carbamic acid benzyl ester (634587-14-7) + 2,3,4,6-tetra-O-acetyl-1S-acetyl-1-thio-β-D-galactopyranose (6806-56-0) → Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(S)-3-benzyloxycarbonylamino-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propylsulfanyl]-tetrahydro-pyran-4-yl ester (634587-17-0)

Guidance literature:

2,3,4,6-tetra-O-acetyl-1S-acetyl-1-thio-β-D-galactopyranose; With hydrazinium monoacetate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

[(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-iodo-propyl]-carbamic acid benzyl ester; With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

Reference yield:

L-2-[(benzyloxycarbonyl)amino]-4-(tert-butyldimethylsilyloxy)-butylaldehyde (634586-95-1) → Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(S)-3-benzyloxycarbonylamino-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propylsulfanyl]-tetrahydro-pyran-4-yl ester (634587-17-0)

Guidance literature:

Multi-step reaction with 6 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

With AD-mix-β; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 2: Sharpless dihydroxylation;

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) → Acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(S)-3-benzyloxycarbonylamino-3-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propylsulfanyl]-tetrahydro-pyran-4-yl ester (634587-17-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: triethylamine

With iodine; triethylamine; triphenylphosphine; In tetrahydrofuran;

DOI:10.1002/anie.200454215

upstream raw materials:

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

2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose

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

[(S)-3-[(2S,4aR,6S,7R,8R,8aR)-7,8-Dihydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylsulfanyl]-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester

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

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