(2S,3R,5S,6R)-2-Allyl-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran

Base Information

Chemical Name:(2S,3R,5S,6R)-2-Allyl-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran
CAS No.:181263-18-3
Molecular Formula:C₃₀H₃₄O₄
Molecular Weight:458.598
Hs Code.:

Synonyms:(2S,3R,5S,6R)-2-Allyl-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran

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Chemical Property of (2S,3R,5S,6R)-2-Allyl-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran

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Technology Process of (2S,3R,5S,6R)-2-Allyl-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran

There total 6 articles about (2S,3R,5S,6R)-2-Allyl-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran 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:

: (2S,3R,5S,6R)-2-Allyl-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ol

: 181263-18-3
(2S,3R,5S,6R)-2-Allyl-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; Yield given;
DOI:10.1021/ja961230+

Reference yield:

: 35303-86-7
(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol

: 181263-18-3
(2S,3R,5S,6R)-2-Allyl-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / tetrahydrofuran

1.2: imidazole / tetrahydrofuran / 1 h / 0 - 20 °C

2.1: Bu₃SnH; AIBN / toluene / 36 h / 110 °C

3.1: 69 percent / aq. HCl / acetic acid / 48 h / 60 °C

4.1: 70 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

5.1: tetrahydrofuran / 1 h / -78 °C

6.1: Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 2 h / 0 °C

With hydrogenchloride; triethylsilane; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; acetic acid; toluene;
DOI:10.1055/s-2001-11398

Reference yield:

: 90124-36-0
2,4,6-tri-O-benzyl-3-deoxy-α-D-methylglucopyranoside

: 181263-18-3
(2S,3R,5S,6R)-2-Allyl-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 4 steps

1: 69 percent / aq. HCl / acetic acid / 48 h / 60 °C

2: 70 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

3: tetrahydrofuran / 1 h / -78 °C

4: Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 2 h / 0 °C

With hydrogenchloride; triethylsilane; oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; acetic acid;
DOI:10.1055/s-2001-11398