((1S,2R,3R)-1-[1,3]Dithiolan-2-ylmethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester

Base Information

• Chemical Name: ((1S,2R,3R)-1-[1,3]Dithiolan-2-ylmethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester
• CAS No.: 128414-13-1
• Molecular Formula: C₁₆H₂₃NO₄S₂
• Molecular Weight: 357.495

Synonyms:((1S,2R,3R)-1-[1,3]Dithiolan-2-ylmethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester

Chemical Property of ((1S,2R,3R)-1-[1,3]Dithiolan-2-ylmethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of ((1S,2R,3R)-1-[1,3]Dithiolan-2-ylmethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester

There total 4 articles about ((1S,2R,3R)-1-[1,3]Dithiolan-2-ylmethyl-2,3-dihydroxy-butyl)-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:

((S)-2-[1,3]Dithiolan-2-yl-1-formyl-ethyl)-carbamic acid benzyl ester (128414-12-0) + acetaldehyde (75-07-0,9002-91-9) → ((1S,2R,3R)-1-[1,3]Dithiolan-2-ylmethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester (128414-13-1)

Guidance literature:

With 2*; In dichloromethane; at 0 ℃; Yield given;

DOI:10.1021/jo00302a005

Reference yield:

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate (87219-29-2) → ((1S,2R,3R)-1-[1,3]Dithiolan-2-ylmethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester (128414-13-1)

Guidance literature:

Multi-step reaction with 4 steps

1: diisobutylaluminium hydride / CH₂Cl₂ / -78 °C

2: BF₃*Et₂O / CH₂Cl₂

3: 85 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide

4: 2Cl₃(THF)6>2*2Cl₆> / CH₂Cl₂ / 0 °C

With pyridine-SO₃ complex; 2*; boron trifluoride diethyl etherate; diisobutylaluminium hydride; triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jo00302a005

Reference yield:

(S)-4-<(Benzyloxycarbonyl)amino>tetrahydrofuran-2-ol (128414-17-5) → ((1S,2R,3R)-1-[1,3]Dithiolan-2-ylmethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester (128414-13-1)

Guidance literature:

Multi-step reaction with 3 steps

1: BF₃*Et₂O / CH₂Cl₂

2: 85 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide

3: 2Cl₃(THF)6>2*2Cl₆> / CH₂Cl₂ / 0 °C

With pyridine-SO₃ complex; 2*; boron trifluoride diethyl etherate; triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jo00302a005

upstream raw materials:

((S)-2-[1,3]Dithiolan-2-yl-1-formyl-ethyl)-carbamic acid benzyl ester

acetaldehyde

benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate

(S)-4-<(Benzyloxycarbonyl)amino>tetrahydrofuran-2-ol

Downstream raw materials:

[(2R,3S)-2-((R)-1-Hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-yl]-carbamic acid benzyl ester

N-benzoyl-D-3-epi-daunosamine

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