(2S,3R,4R)-3-O-benzyl-N-benzyloxycarbonyl-3,4-dihydroxyproline

Base Information

Chemical Name:(2S,3R,4R)-3-O-benzyl-N-benzyloxycarbonyl-3,4-dihydroxyproline
CAS No.:131053-21-9
Molecular Formula:C₂₀H₂₁NO₆
Molecular Weight:371.39
Hs Code.:

Synonyms:(2S,3R,4R)-3-O-benzyl-N-benzyloxycarbonyl-3,4-dihydroxyproline

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Chemical Property of (2S,3R,4R)-3-O-benzyl-N-benzyloxycarbonyl-3,4-dihydroxyproline

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R,4R)-3-O-benzyl-N-benzyloxycarbonyl-3,4-dihydroxyproline

There total 12 articles about (2S,3R,4R)-3-O-benzyl-N-benzyloxycarbonyl-3,4-dihydroxyproline 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: 75.0%

: 131053-19-5
3-O-benzyl-N-benzyloxycarbonyl-2,5-dideoxy-2,5-imino-D-lyxose

: 131053-21-9
(2S,3R,4R)-3-O-benzyl-N-benzyloxycarbonyl-3,4-dihydroxyproline

Guidance literature:: With bromine; barium carbonate; In 1,4-dioxane; water; at 0 ℃; for 24h;
DOI:10.1016/S0957-4166(00)86337-5

Reference yield:

: 101475-83-6
3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

: 131053-21-9
(2S,3R,4R)-3-O-benzyl-N-benzyloxycarbonyl-3,4-dihydroxyproline

Guidance literature:: Multi-step reaction with 10 steps

1: 87 percent / water, HOAc / methanol / 16 h / 50 °C

2: 1.) sodium periodate, 2.) NaBH₄ / 1.) ethanol, water, 3 h, 2.) RT, 8 h

3: 94 percent / pyridine / 2 h / 0 - 20 °C

4: 97 percent / sodium azide / dimethylformamide / 12 h / 70 °C

5: 44 percent / acetyl chloride / 36 h / 0 °C

6: 78 percent / pyridine / CH₂Cl₂ / 1 h / -50 - -30 °C

7: 92.5 percent / H₂ / 5percent Pd/C / ethyl acetate / 4 h / Ambient temperature

8: 90 percent / aq. sodium bicarbonate / diethyl ether / 12 h / Ambient temperature

9: 87 percent / aq. TFA

10: 75 percent / BaCO₃, Br₂ / H₂O; dioxane / 24 h / 0 °C

With pyridine; sodium tetrahydroborate; sodium periodate; sodium azide; water; hydrogen; bromine; sodium hydrogencarbonate; acetic acid; acetyl chloride; barium carbonate; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(00)86337-5

Reference yield:

: 131053-15-1
5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose

: 131053-21-9
(2S,3R,4R)-3-O-benzyl-N-benzyloxycarbonyl-3,4-dihydroxyproline

Guidance literature:: Multi-step reaction with 6 steps

1: 44 percent / acetyl chloride / 36 h / 0 °C

2: 78 percent / pyridine / CH₂Cl₂ / 1 h / -50 - -30 °C

3: 92.5 percent / H₂ / 5percent Pd/C / ethyl acetate / 4 h / Ambient temperature

4: 90 percent / aq. sodium bicarbonate / diethyl ether / 12 h / Ambient temperature

5: 87 percent / aq. TFA

6: 75 percent / BaCO₃, Br₂ / H₂O; dioxane / 24 h / 0 °C

With pyridine; hydrogen; bromine; sodium hydrogencarbonate; acetyl chloride; barium carbonate; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; diethyl ether; dichloromethane; water; ethyl acetate;
DOI:10.1016/S0957-4166(00)86337-5