(2R,3S)-3-Benzyloxycarbonylamino-4-[1,3]dithian-2-ylidene-2-((R)-1-hydroxy-ethyl)-pentanoic acid methyl ester

Base Information

• Chemical Name: (2R,3S)-3-Benzyloxycarbonylamino-4-[1,3]dithian-2-ylidene-2-((R)-1-hydroxy-ethyl)-pentanoic acid methyl ester
• CAS No.: 110918-99-5
• Molecular Formula: C₂₀H₂₇NO₅S₂
• Molecular Weight: 425.57
• Mol file: 110918-99-5.mol

Synonyms:(2R,3S)-3-Benzyloxycarbonylamino-4-[1,3]dithian-2-ylidene-2-((R)-1-hydroxy-ethyl)-pentanoic acid methyl ester

Chemical Property of (2R,3S)-3-Benzyloxycarbonylamino-4-[1,3]dithian-2-ylidene-2-((R)-1-hydroxy-ethyl)-pentanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-Benzyloxycarbonylamino-4-[1,3]dithian-2-ylidene-2-((R)-1-hydroxy-ethyl)-pentanoic acid methyl ester

There total 1 articles about (2R,3S)-3-Benzyloxycarbonylamino-4-[1,3]dithian-2-ylidene-2-((R)-1-hydroxy-ethyl)-pentanoic acid methyl 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:

Methyl (R)-3-hydroxybutyrate (3976-69-0) + N-benzyloxycarbonyl 2-(1,3-dithian-2-yliden)propanimine (110918-98-4) → (2R,3S)-3-Benzyloxycarbonylamino-4-[1,3]dithian-2-ylidene-2-((R)-1-hydroxy-ethyl)-pentanoic acid methyl ester (110918-99-5) + methyl 3-(R,S)-benzyloxycarbonylamino-4-(1,3-dithian-2-yliden)-2-(R)-(1-(R)-hydroxyethyl)-pentanoate (111003-54-4)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1) THF, -78 deg C, 1h, 2) -78 deg C, 1h;

DOI:10.1016/S0040-4039(00)95655-7

Reference yield: 87.0%

(2R,3S)-3-Benzyloxycarbonylamino-4-[1,3]dithian-2-ylidene-2-((R)-1-hydroxy-ethyl)-pentanoic acid methyl ester (110918-99-5) → (8R,9R,10S,11R)-10-Benzyloxycarbonylamino-8,11-dimethyl-7-oxa-1,5-dithia-spiro[5.5]undecane-9-carboxylic acid methyl ester (110919-02-3)

Guidance literature:

With hydrogenchloride; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(00)95655-7

Reference yield:

(2R,3S)-3-Benzyloxycarbonylamino-4-[1,3]dithian-2-ylidene-2-((R)-1-hydroxy-ethyl)-pentanoic acid methyl ester (110918-99-5) → (3R,4R,5S,6R)-4-benzyloxycarbonylamino-3,4,5,6-tetrahydro-5-methoxycarbonyl-3,6-dimethyl-2H-pyran-2-one (110919-04-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / HCl / CH₂Cl₂ / 0 °C

2: 74 percent / NaOMe / methanol; methyl acetate / Heating

3: 91 percent / CuCl₂, CuO / acetone; H₂O

With hydrogenchloride; sodium methylate; copper(II) oxide; copper dichloride; In methanol; dichloromethane; acetic acid methyl ester; water; acetone;

DOI:10.1016/S0040-4039(00)95655-7

upstream raw materials:

Methyl (R)-3-hydroxybutyrate

N-benzyloxycarbonyl 2-(1,3-dithian-2-yliden)propanimine

Downstream raw materials:

(8R,9R,10S,11R)-10-Benzyloxycarbonylamino-8,11-dimethyl-7-oxa-1,5-dithia-spiro[5.5]undecane-9-carboxylic acid methyl ester

(3R,4R,5S,6R)-4-benzyloxycarbonylamino-3,4,5,6-tetrahydro-5-methoxycarbonyl-3,6-dimethyl-2H-pyran-2-one

(8R,9S,10S,11R)-10-Benzyloxycarbonylamino-8,11-dimethyl-7-oxa-1,5-dithia-spiro[5.5]undecane-9-carboxylic acid methyl ester