(1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl) (R_C,S_S)-2-[(benzyloxycarbonyl)amino]-2-methoxycarbonyl ethanesulphinate

Base Information

• Chemical Name: (1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl) (R_C,S_S)-2-[(benzyloxycarbonyl)amino]-2-methoxycarbonyl ethanesulphinate
• CAS No.: 371970-43-3
• Molecular Formula: C₂₄H₃₃NO₁₁S
• Molecular Weight: 543.592

Synonyms:(1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl) (R_C,S_S)-2-[(benzyloxycarbonyl)amino]-2-methoxycarbonyl ethanesulphinate

Chemical Property of (1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl) (R_C,S_S)-2-[(benzyloxycarbonyl)amino]-2-methoxycarbonyl ethanesulphinate

Chemical Property:

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Technology Process of (1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl) (R_C,S_S)-2-[(benzyloxycarbonyl)amino]-2-methoxycarbonyl ethanesulphinate

There total 2 articles about (1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl) (R_C,S_S)-2-[(benzyloxycarbonyl)amino]-2-methoxycarbonyl ethanesulphinate 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%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl) (RC,RS)-2-[(benzyloxycarbonyl)amino]-2-methoxycarbonyl ethanesulphinate (371970-42-2) + (1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl) (RC,SS)-2-[(benzyloxycarbonyl)amino]-2-methoxycarbonyl ethanesulphinate (371970-43-3)

Guidance literature:

With pyridine; In dichloromethane; at -78 ℃; for 0.5h;

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1016/S0957-4166(01)00268-3

Reference yield: 75.0%

N-<(Benzyloxy)carbonyl>-L-cysteine Methyl Ester Sulfinyl Chloride (68836-00-0) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl) (RC,RS)-2-[(benzyloxycarbonyl)amino]-2-methoxycarbonyl ethanesulphinate (371970-42-2) + (1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl) (RC,SS)-2-[(benzyloxycarbonyl)amino]-2-methoxycarbonyl ethanesulphinate (371970-43-3)

Guidance literature:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; With N-ethyl-N,N-diisopropylamine; In toluene; at -78 ℃; for 0.5h;

N-<(Benzyloxy)carbonyl>-L-cysteine Methyl Ester Sulfinyl Chloride; In toluene; at -78 ℃; for 0.5h;

DOI:10.1016/S0957-4166(01)00268-3

Reference yield: 65.0%

methylmagnesium bromide (75-16-1) + (1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl) (RC,SS)-2-[(benzyloxycarbonyl)amino]-2-methoxycarbonyl ethanesulphinate (371970-43-3) → N-(benzyloxycarbonyl)-(R)-S-methyl-S-oxo-L-cysteine methyl ester

Guidance literature:

(1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl) (R_C,S_S)-2-[(benzyloxycarbonyl)amino]-2-methoxycarbonyl ethanesulphinate; With trimethylaluminum; In tetrahydrofuran; at 20 ℃; for 1h;

methylmagnesium bromide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h;

DOI:10.1016/S0957-4166(01)00268-3

upstream raw materials:

N-<(Benzyloxy)carbonyl>-L-cysteine Methyl Ester Sulfinyl Chloride

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

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