(S)-4-[(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-tert-butoxycarbonylamino-pent-4-enoic acid methyl ester

Base Information

Chemical Name:(S)-4-[(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-tert-butoxycarbonylamino-pent-4-enoic acid methyl ester
CAS No.:1053478-30-0
Molecular Formula:C₃₇H₅₅NO₈Si
Molecular Weight:669.931
Hs Code.:

(S)-4-[(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-tert-butoxycarbonylamino-pent-4-enoic acid methyl ester

Synonyms:(S)-4-[(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-tert-butoxycarbonylamino-pent-4-enoic acid methyl ester

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Chemical Property of (S)-4-[(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-tert-butoxycarbonylamino-pent-4-enoic acid methyl ester

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Technology Process of (S)-4-[(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-tert-butoxycarbonylamino-pent-4-enoic acid methyl ester

There total 14 articles about (S)-4-[(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-tert-butoxycarbonylamino-pent-4-enoic acid methyl 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: 52.0%

: (R)-(2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)zinc(II)iodide

: 1054647-37-8
Trifluoro-methanesulfonic acid 1-[(2R,3R,4R,5R)-4,5-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-vinyl ester

: 1053478-30-0
(S)-4-[(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-tert-butoxycarbonylamino-pent-4-enoic acid methyl ester

Guidance literature:: bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 60 ℃; for 2h;
DOI:10.1021/ol015798l

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 1053478-30-0
(S)-4-[(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-tert-butoxycarbonylamino-pent-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 5 h / 0 °C

1.2: 85 percent / CSA / CH₂Cl₂; methanol / 1 h / 0 °C

2.1: SO₃*Pyr; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

3.1: 5.87 g / NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

4.1: 9-BBN / tetrahydrofuran / 2 h / 0 - 20 °C

4.2: 95 percent / NaHCO₃; H₂O₂ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

5.1: SO₃*Pyr; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1.5 h / 0 °C

6.1: tetrahydrofuran; diethyl ether / 0.58 h / -78 - 0 °C

7.1: 4.64 g / TPAP; N-methylmorpholine N-oxide; 4 Angstroem MS / CH₂Cl₂ / 3 h / 20 °C

8.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -78 - 0 °C

9.1: 52 percent / PdCl₂(PPh₃)2 / tetrahydrofuran; various solvent(s) / 2 h / 60 °C

With 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; pyridine-SO₃ complex; 4 Angstroem MS; sodium hexamethyldisilazane; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; 3.1: Wittig reaction / 6.1: Grignard reaction;
DOI:10.1021/ol015798l

Reference yield:

: 100-39-0
benzyl bromide

: 1053478-30-0
(S)-4-[(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2-tert-butoxycarbonylamino-pent-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: NaH / dimethylformamide; various solvent(s) / 0 - 20 °C

2.1: 1.63 g / CSA / CH₂Cl₂; methanol / 20 h / 0 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 5 h / 0 °C

3.2: 85 percent / CSA / CH₂Cl₂; methanol / 1 h / 0 °C

4.1: SO₃*Pyr; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

5.1: 5.87 g / NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

6.1: 9-BBN / tetrahydrofuran / 2 h / 0 - 20 °C

6.2: 95 percent / NaHCO₃; H₂O₂ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

7.1: SO₃*Pyr; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1.5 h / 0 °C

8.1: tetrahydrofuran; diethyl ether / 0.58 h / -78 - 0 °C

9.1: 4.64 g / TPAP; N-methylmorpholine N-oxide; 4 Angstroem MS / CH₂Cl₂ / 3 h / 20 °C

10.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -78 - 0 °C

11.1: 52 percent / PdCl₂(PPh₃)2 / tetrahydrofuran; various solvent(s) / 2 h / 60 °C

With 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; pyridine-SO₃ complex; 4 Angstroem MS; camphor-10-sulfonic acid; sodium hexamethyldisilazane; potassium hexamethylsilazane; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 5.1: Wittig reaction / 8.1: Grignard reaction;
DOI:10.1021/ol015798l