(2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-methoxy-benzyloxy)-2-vinyl-tetrahydro-pyran

Base Information

Chemical Name:(2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-methoxy-benzyloxy)-2-vinyl-tetrahydro-pyran
CAS No.:688800-04-6
Molecular Formula:C₃₀H₃₄O₆
Molecular Weight:490.596
Hs Code.:

Synonyms:(2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-methoxy-benzyloxy)-2-vinyl-tetrahydro-pyran

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Chemical Property of (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-methoxy-benzyloxy)-2-vinyl-tetrahydro-pyran

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Technology Process of (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-methoxy-benzyloxy)-2-vinyl-tetrahydro-pyran

There total 5 articles about (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-methoxy-benzyloxy)-2-vinyl-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:

: 57783-73-0,79218-74-9,81561-89-9,86172-90-9,79218-87-4
methyl 3,4-di-O-benzyl-α-D-mannopyranoside

: 688800-04-6
(2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-methoxy-benzyloxy)-2-vinyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / imidazole / CH₂Cl₂ / 1 h

2: 73 percent / NaH / tetrahydrofuran / 4 h

3: 74 percent / n-Bu₄NF / tetrahydrofuran / 1 h

4: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: 1.3 g / diethyl ether / 0.5 h / -40 °C

With 1H-imidazole; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 4: Swern oxidation;
DOI:10.1016/j.tet.2004.02.017

Reference yield:

: 688799-98-6
methyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-D-mannopyranoside

: 688800-04-6
(2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-methoxy-benzyloxy)-2-vinyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 4 steps

1: 73 percent / NaH / tetrahydrofuran / 4 h

2: 74 percent / n-Bu₄NF / tetrahydrofuran / 1 h

3: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

4: 1.3 g / diethyl ether / 0.5 h / -40 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 3: Swern oxidation;
DOI:10.1016/j.tet.2004.02.017

Reference yield:

: 688800-00-2
methyl 3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-O-(p-methoxybenzyl)-α-D-mannopyranoside

: 688800-04-6
(2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-methoxy-5-(4-methoxy-benzyloxy)-2-vinyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 3 steps

1: 74 percent / n-Bu₄NF / tetrahydrofuran / 1 h

2: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

3: 1.3 g / diethyl ether / 0.5 h / -40 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 2: Swern oxidation;
DOI:10.1016/j.tet.2004.02.017