(2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide

Base Information

Chemical Name:(2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide
CAS No.:697288-29-2
Molecular Formula:C₁₃H₁₈N₂O₄S
Molecular Weight:298.363
Hs Code.:

Synonyms:(2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide

Suppliers and Price of (2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide

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Chemical Property of (2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide

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Technology Process of (2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide

There total 9 articles about (2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide 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: 70.0%

: 103-72-0
phenyl isothiocyanate

: 59920-31-9
2,5-dideoxy-2,5-imino-D-mannitol

: 697288-29-2
(2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide

Guidance literature:: With pyridine; at 20 ℃; for 24h;
DOI:10.1021/jo0499221

Reference yield:

: 25018-67-1
1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose

: 697288-29-2
(2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / pyridine / 4 h / 20 °C

2: 85 percent / acetic acid / H₂O / 3 h / 50 °C

3: 90 percent / pyridine / 1.5 h / -65 °C

4: 98 percent / iodine; triphenylphosphine; imidazole / toluene / 70 °C

5: 91 percent / sodium azide; HMPT / 80 °C

6: sodium methoxide / methanol

7: 1.08 g / trifluoroacetic acid / H₂O

8: 89 percent / hydrogen / Pd/C / methanol; H₂O / 24 h / 3000.24 Torr

9: 70 percent / pyridine / 24 h / 20 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; hydrogen; iodine; sodium methylate; acetic acid; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In methanol; water; toluene;
DOI:10.1021/jo0499221

Reference yield:

: 99648-49-4
3-O-benzoyl-1,2-O-isopropylidene-β-D-fructopyranose

: 697288-29-2
(2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-hydroxymethyl-pyrrolidine-1-carbothioic acid phenylamide

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / pyridine / 1.5 h / -65 °C

2: 98 percent / iodine; triphenylphosphine; imidazole / toluene / 70 °C

3: 91 percent / sodium azide; HMPT / 80 °C

4: sodium methoxide / methanol

5: 1.08 g / trifluoroacetic acid / H₂O

6: 89 percent / hydrogen / Pd/C / methanol; H₂O / 24 h / 3000.24 Torr

7: 70 percent / pyridine / 24 h / 20 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; hydrogen; iodine; sodium methylate; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In methanol; water; toluene;
DOI:10.1021/jo0499221