(2R,3aR,6R,7R,7aS)-6,7-Bis-benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3aR,6R,7R,7aS)-6,7-Bis-benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester
CAS No.:340999-67-9
Molecular Formula:C₃₂H₄₁NO₁₀
Molecular Weight:599.678
Hs Code.:

(2R,3aR,6R,7R,7aS)-6,7-Bis-benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Synonyms:(2R,3aR,6R,7R,7aS)-6,7-Bis-benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

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Chemical Property of (2R,3aR,6R,7R,7aS)-6,7-Bis-benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

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Technology Process of (2R,3aR,6R,7R,7aS)-6,7-Bis-benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

There total 19 articles about (2R,3aR,6R,7R,7aS)-6,7-Bis-benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic 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: 43.0%

: (S)-3-((3aR,6R,7R,7aS)-6,7-Bis-benzyloxy-2-hydroxymethyl-hexahydro-furo[3,2-b]pyran-2-yl)-2-tert-butoxycarbonylamino-propionic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 340999-67-9
(2R,3aR,6R,7R,7aS)-6,7-Bis-benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

: 340999-68-0
(2S,3aR,6R,7R,7aS)-6,7-Bis-benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Guidance literature:: (S)-3-((3aR,6R,7R,7aS)-6,7-Bis-benzyloxy-2-hydroxymethyl-hexahydro-furo[3,2-b]pyran-2-yl)-2-tert-butoxycarbonylamino-propionic acid; With tetrapropylammonium perruthennate; 4 Angstroem MS; 4-methylmorpholine N-oxide; In acetonitrile; at 20 ℃; for 46h;

diazomethyl-trimethyl-silane; In methanol; hexane; at 20 ℃; for 18h; Further stages.;
DOI:10.1021/ol015798l

Reference yield:

: 100-39-0
benzyl bromide

: 340999-67-9
(2R,3aR,6R,7R,7aS)-6,7-Bis-benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 17 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

12.1: 83 percent / n-Bu₄NF / tetrahydrofuran / 5 h / 20 °C

13.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 10 h / 20 °C

14.1: 665.7 mg / NaBH₄ / tetrahydrofuran; methanol / -78 - 0 °C

15.1: 88 percent / m-CPBA / CH₂Cl₂; aq. phosphate buffer / 3 h / 20 °C / pH 7.0

16.1: CSA / CH₂Cl₂ / 0.5 h / 20 °C

16.2: 46 percent / aq. NaOH / tetrahydrofuran / 0.5 h / 20 °C

17.1: TPAP; N-methylmorpholine N-oxide; 4 Angstroem MS / acetonitrile / 46 h / 20 °C

17.2: 43 percent / methanol; hexane / 18 h / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; pyridine-SO₃ complex; 4 Angstroem MS; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: Wittig reaction / 8.1: Grignard reaction;
DOI:10.1021/ol015798l

Reference yield:

: 150571-93-0
1,5-anhydro-2,3-dideoxy-4,6-O-(phenylmethylene)-D-erythro-hex-1-enitol

: 340999-67-9
(2R,3aR,6R,7R,7aS)-6,7-Bis-benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 18 steps

1.1: 79 percent / OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 24 h / 20 °C

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

3.1: 1.63 g / CSA / CH₂Cl₂; methanol / 20 h / 0 °C

4.1: 2,6-lutidine / CH₂Cl₂ / 5 h / 0 °C

4.2: 85 percent / CSA / CH₂Cl₂; methanol / 1 h / 0 °C

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

6.1: 5.87 g / NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

7.1: 9-BBN / tetrahydrofuran / 2 h / 0 - 20 °C

7.2: 95 percent / NaHCO₃; H₂O₂ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

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

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

10.1: 4.64 g / TPAP; N-methylmorpholine N-oxide; 4 Angstroem MS / CH₂Cl₂ / 3 h / 20 °C

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

12.1: 52 percent / PdCl₂(PPh₃)2 / tetrahydrofuran; various solvent(s) / 2 h / 60 °C

13.1: 83 percent / n-Bu₄NF / tetrahydrofuran / 5 h / 20 °C

14.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 10 h / 20 °C

15.1: 665.7 mg / NaBH₄ / tetrahydrofuran; methanol / -78 - 0 °C

16.1: 88 percent / m-CPBA / CH₂Cl₂; aq. phosphate buffer / 3 h / 20 °C / pH 7.0

17.1: CSA / CH₂Cl₂ / 0.5 h / 20 °C

17.2: 46 percent / aq. NaOH / tetrahydrofuran / 0.5 h / 20 °C

18.1: TPAP; N-methylmorpholine N-oxide; 4 Angstroem MS / acetonitrile / 46 h / 20 °C

18.2: 43 percent / methanol; hexane / 18 h / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; tetrapropylammonium perruthennate; pyridine-SO₃ complex; 4 Angstroem MS; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 6.1: Wittig reaction / 9.1: Grignard reaction;
DOI:10.1021/ol015798l