(2R,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde

Base Information

• Chemical Name: (2R,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde
• CAS No.: 349552-53-0
• Molecular Formula: C₂₂H₃₆O₄Si
• Molecular Weight: 392.611

Synonyms:(2R,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde

Chemical Property of (2R,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde

There total 7 articles about (2R,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde 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: 100.0%

(2S,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propan-1-ol (349552-52-9) → (2R,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde (349552-53-0)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃; for 0.583333h;

DOI:10.1055/s-2001-13387

Reference yield:

(2'R,3'S)-<3'-(tert-butyldimethylsilyloxy)tetrahydropyran-2'-yl>methanol (138750-71-7,125877-82-9) → (2R,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde (349552-53-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.55 h / -78 - -18 °C

2.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 2.08 h / -78 - 0 °C

2.2: CH₂Cl₂ / 2.33 h / -78 - -20 °C

3.1: 100 percent / NaBH₄ / tetrahydrofuran; H₂O / 2.8 h / 25 °C

4.1: 100 percent / DMAP; pyridine / CH₂Cl₂ / 2.7 h / 23 °C

5.1: 75 percent / NaH; TBAI / tetrahydrofuran / 20 h / 24 °C

6.1: 93 percent / PPTS / methanol; CH₂Cl₂ / 5 h / 23 °C

7.1: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.58 h / -78 - 0 °C

With pyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Swern oxidation / 2.1: Evans aldol reaction / 7.1: Swern oxidation;

DOI:10.1055/s-2001-13387

Reference yield:

(2'S,3'S)-3'-(tert-butyldimethylsiloxy)-tetrahydropyran-2'-carbaldehyde (125877-83-0) → (2R,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde (349552-53-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 2.08 h / -78 - 0 °C

1.2: CH₂Cl₂ / 2.33 h / -78 - -20 °C

2.1: 100 percent / NaBH₄ / tetrahydrofuran; H₂O / 2.8 h / 25 °C

3.1: 100 percent / DMAP; pyridine / CH₂Cl₂ / 2.7 h / 23 °C

4.1: 75 percent / NaH; TBAI / tetrahydrofuran / 20 h / 24 °C

5.1: 93 percent / PPTS / methanol; CH₂Cl₂ / 5 h / 23 °C

6.1: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.58 h / -78 - 0 °C

With pyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Evans aldol reaction / 6.1: Swern oxidation;

DOI:10.1055/s-2001-13387

upstream raw materials:

(2S,3R)-3-Benzyloxy-3-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propan-1-ol

(2'R,3'S)-<3'-(tert-butyldimethylsilyloxy)tetrahydropyran-2'-yl>methanol

(2'S,3'S)-3'-(tert-butyldimethylsiloxy)-tetrahydropyran-2'-carbaldehyde

(1R,2S)-1-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-2-methyl-propane-1,3-diol

Downstream raw materials:

(4aS,6R,8R,9R,9aS)-9-Benzyloxy-6-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-ylmethyl)-8-methyl-hexahydro-1,5-dioxa-benzocyclohepten-7-one

(4aS,6R,7S,8S,9R,9aS)-9-Benzyloxy-6-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-ylmethyl)-8-methyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol

(4S,5R)-5-Benzyloxy-1-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-yl)-3-hydroxy-5-((2S,3S)-3-hydroxy-tetrahydro-pyran-2-yl)-4-methyl-pentan-2-one

(4S,5R)-5-Benzyloxy-1-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-yl)-5-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-3-hydroxy-4-methyl-pentan-2-one

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