bis<(3S,4R)-3-benzyloxycarbonylamino-3-methoxy-1-<(1R)-methoxycarbonyl-2-methylprop-2-enyl>-2-oxoazetidin-4-yl> disulfide

Base Information

• Chemical Name: bis<(3S,4R)-3-benzyloxycarbonylamino-3-methoxy-1-<(1R)-methoxycarbonyl-2-methylprop-2-enyl>-2-oxoazetidin-4-yl> disulfide
• CAS No.: 88019-36-7
• Molecular Formula: C₃₆H₄₂N₄O₁₂S₂
• Molecular Weight: 786.881
• Mol file: 88019-36-7.mol

Synonyms:bis<(3S,4R)-3-benzyloxycarbonylamino-3-methoxy-1-<(1R)-methoxycarbonyl-2-methylprop-2-enyl>-2-oxoazetidin-4-yl> disulfide

Chemical Property of bis<(3S,4R)-3-benzyloxycarbonylamino-3-methoxy-1-<(1R)-methoxycarbonyl-2-methylprop-2-enyl>-2-oxoazetidin-4-yl> disulfide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of bis<(3S,4R)-3-benzyloxycarbonylamino-3-methoxy-1-<(1R)-methoxycarbonyl-2-methylprop-2-enyl>-2-oxoazetidin-4-yl> disulfide

There total 4 articles about bis<(3S,4R)-3-benzyloxycarbonylamino-3-methoxy-1-<(1R)-methoxycarbonyl-2-methylprop-2-enyl>-2-oxoazetidin-4-yl> disulfide 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: 59.8%

(3S,4R)-3-benzyloxycarbonylamino-3-methoxy-1-<(1R)-methoxycarbonyl-2-methylprop-2-enyl>-4-(benzothiazol-2-yl-dithio)-2-azetidinone (88019-35-6) → bis<(3S,4R)-3-benzyloxycarbonylamino-3-methoxy-1-<(1R)-methoxycarbonyl-2-methylprop-2-enyl>-2-oxoazetidin-4-yl> disulfide (88019-36-7)

Guidance literature:

With hydrogen; nickel; In tetrahydrofuran; for 0.25h; Ambient temperature;

DOI:10.1248/cpb.31.2200

Reference yield: 10.5%

2-Mercaptobenzothiazole (149-30-4,118090-09-8) + (2S,5R,6S)-6-Benzyloxycarbonylamino-6-methoxy-3,3-dimethyl-4,7-dioxo-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester (78114-99-5) → (3S,4R)-3-benzyloxycarbonylamino-3-methoxy-1-<(1R)-methoxycarbonyl-2-methylprop-2-enyl>-4-(benzothiazol-2-yl-dithio)-2-azetidinone (88019-35-6) + bis<(3S,4R)-3-benzyloxycarbonylamino-3-methoxy-1-<(1R)-methoxycarbonyl-2-methylprop-2-enyl>-2-oxoazetidin-4-yl> disulfide (88019-36-7)

Guidance literature:

In 1,4-dioxane; for 3.5h; Heating;

DOI:10.1248/cpb.31.2200

Reference yield:

6β-benzyloxycarbonylamino-1ξ-oxo-1λ4-penicillanic acid methyl ester (96947-34-1) → bis<(3S,4R)-3-benzyloxycarbonylamino-3-methoxy-1-<(1R)-methoxycarbonyl-2-methylprop-2-enyl>-2-oxoazetidin-4-yl> disulfide (88019-36-7)

Guidance literature:

Multi-step reaction with 3 steps

1: tert-butyl hypochlorite

2: 25.9 percent / dioxane / 3.5 h / Heating

3: 59.8 percent / H₂ / Raney nickel / tetrahydrofuran / 0.25 h / Ambient temperature

With tert-butylhypochlorite; hydrogen; nickel; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1248/cpb.31.2200

upstream raw materials:

2-Mercaptobenzothiazole

(2S,5R,6S)-6-Benzyloxycarbonylamino-6-methoxy-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

(3S,4R)-3-benzyloxycarbonylamino-3-methoxy-1-<(1R)-methoxycarbonyl-2-methylprop-2-enyl>-4-(benzothiazol-2-yl-dithio)-2-azetidinone

6β-benzyloxycarbonylamino-1ξ-oxo-1λ⁴-penicillanic acid methyl ester