Benzyl-[(S)-3-[(2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-6-sulfonyl]-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: Benzyl-[(S)-3-[(2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-6-sulfonyl]-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester
• CAS No.: 762262-40-8
• Molecular Formula: C₆₅H₈₅NO₁₂S
• Molecular Weight: 1104.46
• Mol file: 762262-40-8.mol

Synonyms:Benzyl-[(S)-3-[(2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-6-sulfonyl]-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester

Chemical Property of Benzyl-[(S)-3-[(2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-6-sulfonyl]-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl-[(S)-3-[(2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-6-sulfonyl]-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester

There total 18 articles about Benzyl-[(S)-3-[(2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-6-sulfonyl]-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl 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: 93.0%

Benzyl-[(S)-3-[(2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-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 (762262-39-5) → Benzyl-[(S)-3-[(2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-6-sulfonyl]-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester (762262-40-8)

Guidance literature:

With magnesium monoperoxyphthalate hexahydrate; In tetrahydrofuran; ethanol; water; at 60 ℃;

DOI:10.1002/anie.200454215

Reference yield:

L-2-[(benzyloxycarbonyl)amino]-4-(tert-butyldimethylsilyloxy)-butylaldehyde (634586-95-1) → Benzyl-[(S)-3-[(2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-6-sulfonyl]-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester (762262-40-8)

Guidance literature:

Multi-step reaction with 10 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

With AD-mix-β; 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; 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) → Benzyl-[(S)-3-[(2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-6-sulfonyl]-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester (762262-40-8)

Guidance literature:

Multi-step reaction with 6 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

With iodine; sodium methylate; sodium hydride; toluene-4-sulfonic acid; magnesium monoperoxyphthalate hexahydrate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/anie.200454215

upstream raw materials:

Benzyl-[(S)-3-[(2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-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

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:

Benzyl-[(S)-3-[(2S,4aR,7R,8S,8aS)-7,8-bis-benzyloxy-2-(4-methoxy-phenyl)-tetrahydro-pyrano[3,2-d][1,3]dioxin-(6Z)-ylidene]-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl 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

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,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