(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsiloxy)-4-(1-imidazolylcarbothioyloxy)-piperidine

Base Information

Chemical Name:(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsiloxy)-4-(1-imidazolylcarbothioyloxy)-piperidine
CAS No.:664978-86-3
Molecular Formula:C₂₉H₄₇N₃O₅SSi₂
Molecular Weight:605.946
Hs Code.:

Synonyms:(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsiloxy)-4-(1-imidazolylcarbothioyloxy)-piperidine

Suppliers and Price of (3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsiloxy)-4-(1-imidazolylcarbothioyloxy)-piperidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsiloxy)-4-(1-imidazolylcarbothioyloxy)-piperidine

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsiloxy)-4-(1-imidazolylcarbothioyloxy)-piperidine

There total 13 articles about (3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsiloxy)-4-(1-imidazolylcarbothioyloxy)-piperidine 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: 87.0%

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 497181-37-0
(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsilyloxy)piperidin-4-ol

: 664978-86-3
(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsiloxy)-4-(1-imidazolylcarbothioyloxy)-piperidine

Guidance literature:: With dmap; In tetrahydrofuran; at 80 ℃; for 21h;
DOI:10.3987/com-03-s(p)34

Reference yield:

: 57492-90-7
1-O-benzoyl-2,3-O-isopropylidene-α-D-mannofuranoside

: 664978-86-3
(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsiloxy)-4-(1-imidazolylcarbothioyloxy)-piperidine

Guidance literature:: Multi-step reaction with 10 steps

1: sodium periodate / diethyl ether; H₂O / 1 h / 20 °C

2: 23.3 g / NaBH₄ / methanol / 0.5 h / 0 °C

3: 100 percent / pyridine / 13 h / 20 °C

4: 85 percent / NaN₃ / dimethylformamide / 16 h / 80 °C

5: 97 percent / aq. NaOH / methanol / 0.5 h / 20 °C

6: H₂ / Pd(OH)2 / methanol / 14 h / 20 °C / 760 Torr

7: aq. NaHCO₃ / diethyl ether / 21 h / 20 °C

8: 92 percent / aq. AcOH / 18 h / 90 °C

9: 87 percent / Et₃N / dimethylformamide / 2 h / 20 °C

10: 87 percent / DMAP / tetrahydrofuran / 21 h / 80 °C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; sodium azide; hydrogen; sodium hydrogencarbonate; acetic acid; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide;
DOI:10.3987/com-03-s(p)34

Reference yield:

: 57526-34-8
(+)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranos-3-yl benzoate

: 664978-86-3
(3R,5R)-1-benzyloxycarbonyl-3,5-bis(tert-butyldimethylsiloxy)-4-(1-imidazolylcarbothioyloxy)-piperidine

Guidance literature:: Multi-step reaction with 11 steps

1: 100 percent / aq. AcOH / 48 h / 20 °C

2: sodium periodate / diethyl ether; H₂O / 1 h / 20 °C

3: 23.3 g / NaBH₄ / methanol / 0.5 h / 0 °C

4: 100 percent / pyridine / 13 h / 20 °C

5: 85 percent / NaN₃ / dimethylformamide / 16 h / 80 °C

6: 97 percent / aq. NaOH / methanol / 0.5 h / 20 °C

7: H₂ / Pd(OH)2 / methanol / 14 h / 20 °C / 760 Torr

8: aq. NaHCO₃ / diethyl ether / 21 h / 20 °C

9: 92 percent / aq. AcOH / 18 h / 90 °C

10: 87 percent / Et₃N / dimethylformamide / 2 h / 20 °C

11: 87 percent / DMAP / tetrahydrofuran / 21 h / 80 °C

With pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; sodium azide; hydrogen; sodium hydrogencarbonate; acetic acid; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide;
DOI:10.3987/com-03-s(p)34