(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal

Base Information

• Chemical Name: (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal
• CAS No.: 289666-94-0
• Molecular Formula: C₃₄H₄₄O₆Si
• Molecular Weight: 576.805

Synonyms:(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal

Chemical Property of (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal

There total 18 articles about (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal 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: 97.0%

(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanol (289667-09-0) → (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal (289666-94-0)

Guidance literature:

With pyridine-SO₃ complex; triethylamine; In dimethyl sulfoxide; for 2.5h;

DOI:10.1021/ol052943c DOI:10.1021/jo060803q

Reference yield:

(+)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanol (289666-90-6) → (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal (289666-94-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -30 °C

2.1: Yb(OTf)3 / CH₂Cl₂ / 48 h / 20 °C

3.1: NaH / tetrahydrofuran / 0 - 20 °C

3.2: 95 percent / tetrahydrofuran / 0 - 20 °C

4.1: 100 percent / DIBAL-H / tetrahydrofuran / 1 h / 0 °C

5.1: 97 percent / SO₃*Py; Et₃N / dimethylsulfoxide / 2.5 h

With oxalyl dichloride; pyridine-SO₃ complex; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 1.1: Swern oxidation;

DOI:10.1021/jo060803q

Reference yield:

(2RS,3R,4R)-3-benzyloxy-4,5-isopropylidenedioxy-1,2-pentanediol → (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal (289666-94-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 61 percent / DMAP; Et₃N / CH₂Cl₂ / 10 h / 20 °C

2.1: 98 percent / AcOH; H₂O / tetrahydrofuran / 6 h / 55 °C

3.1: 89 percent / pyridine / CH₂Cl₂ / 10 h / 20 °C

4.1: 88 percent / P₂O₅ / CH₂Cl₂ / 1.5 h

5.1: 99 percent / DIBALH / tetrahydrofuran / 1 h / 0 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -30 °C

7.1: Yb(OTf)3 / CH₂Cl₂ / 48 h / 20 °C

8.1: NaH / tetrahydrofuran / 0 - 20 °C

8.2: 95 percent / tetrahydrofuran / 0 - 20 °C

9.1: 100 percent / DIBAL-H / tetrahydrofuran / 1 h / 0 °C

10.1: 97 percent / SO₃*Py; Et₃N / dimethylsulfoxide / 2.5 h

With pyridine; dmap; oxalyl dichloride; pyridine-SO₃ complex; water; phosphorus pentoxide; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 6.1: Swern oxidation;

DOI:10.1021/jo060803q

upstream raw materials:

(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanol

(R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol

(+)-(2R,3R)-1,2-O-isopropylidene-4-pentyne-1,2,3-triol

(2R,3R)-3-O-benzyl-1,2-O-isopropylidene-4-pentene-1,2,3-triol

Downstream raw materials:

(1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

(+)-(2R,3R,4R,5S)-1-tert-butyldiphenylsilyloxy-6,6-dimethyl-3-hydroxy-5-methoxy-2,4-methylenedioxyoct-7-en-3-ol

(1R,5R,6R,8RS,10S)-8-acetoxy-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-2,4,7-trioxabicyclo[4.4.0]decane

(+)-(1R,5R,6R,8R,10S)-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

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