methyl 5-[(1S,2S,5R)-7-oxo-3-thia-6,8-diazabicyclo[3.3.0]oct-2-yl]pent anoate

Base Information

• Chemical Name: methyl 5-[(1S,2S,5R)-7-oxo-3-thia-6,8-diazabicyclo[3.3.0]oct-2-yl]pent anoate
• CAS No.: 60562-11-0
• Molecular Formula: C₁₁H₁₈N₂O₃S
• Molecular Weight: 258.342
• Mol file: 60562-11-0.mol

Synonyms:1H-Thieno[3,4-d]imidazole-4-pentanoicacid, hexahydro-2-oxo-, methyl ester, (3aa,4b,6aa)- (9CI);1H-Thieno[3,4-d]imidazole-4-pentanoic acid, hexahydro-2-oxo-, methyl ester, (3aa,4b,6aa)-(?à)-; (?à)-Biotin methyl ester; DL-Biotin methyl ester

Chemical Property of methyl 5-[(1S,2S,5R)-7-oxo-3-thia-6,8-diazabicyclo[3.3.0]oct-2-yl]pent anoate

Chemical Property:

• Melting Point: 127-129 °C
• Boiling Point: 476.4±30.0 °C(Predicted)
• PKA: 13.88±0.40(Predicted)
• PSA: 92.73000
• Density: 1.184±0.06 g/cm3(Predicted)
• LogP: 1.54280

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl5-((3aR,4R,6aS)-rel-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-[(1S,2S,5R)-7-oxo-3-thia-6,8-diazabicyclo[3.3.0]oct-2-yl]pent anoate

There total 31 articles about methyl 5-[(1S,2S,5R)-7-oxo-3-thia-6,8-diazabicyclo[3.3.0]oct-2-yl]pent anoate 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:

5-bromopentanoic acid (2067-33-6) → (+/-)-biotin methyl ester (608-16-2,60562-11-0)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) NaI, (ii) /BRN= 773645/, H₂SO₄

2: (i) <1,10>phenanthroline, MeLi, (ii) /BRN= 1930768/, (iii) TiCl₃, /BRN= 1098229/, (iv) /BRN= 1098229/, aq. H₂SO₄, (v) 1,4-diazabicyclo<2.2.2>octane, RhCl(PPh₃)3

3: aq. HCl / methanol

With hydrogenchloride; In methanol;

DOI:10.1021/ja00473a038

Reference yield:

5-iodovaleric acid tert-butyl ester (56198-37-9) → (+/-)-biotin methyl ester (608-16-2,60562-11-0)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) <1,10>phenanthroline, MeLi, (ii) /BRN= 1930768/, (iii) TiCl₃, /BRN= 1098229/, (iv) /BRN= 1098229/, aq. H₂SO₄, (v) 1,4-diazabicyclo<2.2.2>octane, RhCl(PPh₃)3

2: aq. HCl / methanol

With hydrogenchloride; In methanol;

DOI:10.1021/ja00473a038

Reference yield:

(3aα,6aα)-1,3-dibenzylhexahydro-1H-thieno<3,4-d>imidazol-2(3H)-one (56198-34-6) → (+/-)-biotin methyl ester (608-16-2,60562-11-0)

Guidance literature:

Multi-step reaction with 3 steps

1: NaIO₄ / methanol; H₂O

2: (i) <1,10>phenanthroline, MeLi, (ii) /BRN= 1930768/, (iii) TiCl₃, /BRN= 1098229/, (iv) /BRN= 1098229/, aq. H₂SO₄, (v) 1,4-diazabicyclo<2.2.2>octane, RhCl(PPh₃)3

3: aq. HCl / methanol

With hydrogenchloride; sodium periodate; In methanol; water;

DOI:10.1021/ja00473a038

upstream raw materials:

2-(4-methoxy-butyl)-tetrahydro-thiophene-3,4-dicarboxylic acid diethyl ester

5-(2-oxo-1,3-dipropenyl-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid methyl ester

5-(1,3-dibenzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoic acid

2-oxo-2,3-dihydro-4-(δ-methoxycarbonylbutyl)-1H-thieno<3,4-d>imidazole

Downstream raw materials:

(+/-)-biotin

cis-3,4-di(methoxycarbonylamino)-2-(δ-methoxycarbonylbutyl)thiophane

Refernces

• 1、 Whitney, Ralph Allen. "A total synthesis of (+/-)-biotin". . p. 1158 - 1160. Retrieved 2007/10/02.
• 2、 Confalone, Pat N.,Pizzolato, Giacomo,Confalone, Dianne Lollar,Uskokovic Milan R.. "Olefinic Nitrone and Nitrile Oxide Cycloadditions. A Short Stereospecific Synthesis of Biotin from Cycloheptene". . p. 1954 - 1960. Retrieved 2007/10/02.