p-methoxybenzyl 6,7,8-trideoxy-5-O-benzyl-2,3-O-(1-methylethylidene)-α-D-manno-oct-7-enofuranoside

Base Information

Chemical Name:p-methoxybenzyl 6,7,8-trideoxy-5-O-benzyl-2,3-O-(1-methylethylidene)-α-D-manno-oct-7-enofuranoside
CAS No.:333717-21-8
Molecular Formula:C₂₆H₃₂O₆
Molecular Weight:440.536
Hs Code.:

Synonyms:p-methoxybenzyl 6,7,8-trideoxy-5-O-benzyl-2,3-O-(1-methylethylidene)-α-D-manno-oct-7-enofuranoside

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Chemical Property of p-methoxybenzyl 6,7,8-trideoxy-5-O-benzyl-2,3-O-(1-methylethylidene)-α-D-manno-oct-7-enofuranoside

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Technology Process of p-methoxybenzyl 6,7,8-trideoxy-5-O-benzyl-2,3-O-(1-methylethylidene)-α-D-manno-oct-7-enofuranoside

There total 6 articles about p-methoxybenzyl 6,7,8-trideoxy-5-O-benzyl-2,3-O-(1-methylethylidene)-α-D-manno-oct-7-enofuranoside 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%

: 100-39-0
benzyl bromide

: 333717-23-0
(R)-1-[(3aS,4R,6S,6aS)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-but-3-en-1-ol

: 333717-21-8
p-methoxybenzyl 6,7,8-trideoxy-5-O-benzyl-2,3-O-(1-methylethylidene)-α-D-manno-oct-7-enofuranoside

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; at 20 ℃; for 16h;
DOI:10.1021/jo001447t

Reference yield:

: 1-[(3aS,4R,6S,6aS)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-ethane-1,2-diol

: 333717-21-8
p-methoxybenzyl 6,7,8-trideoxy-5-O-benzyl-2,3-O-(1-methylethylidene)-α-D-manno-oct-7-enofuranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / NaIO₄ / H₂O; methanol / 1 h / 20 °C

2: 77 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -78 °C

3: 97 percent / NaH; n-Bu₄NI / 16 h / 20 °C

With sodium periodate; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; In methanol; dichloromethane; water;
DOI:10.1021/jo001447t

Reference yield:

: (3aS,4R,6S,6aS)-4-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

: 333717-21-8
p-methoxybenzyl 6,7,8-trideoxy-5-O-benzyl-2,3-O-(1-methylethylidene)-α-D-manno-oct-7-enofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 10.5 g / HCl / H₂O; methanol / 3 h

2: 97 percent / NaIO₄ / H₂O; methanol / 1 h / 20 °C

3: 77 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -78 °C

4: 97 percent / NaH; n-Bu₄NI / 16 h / 20 °C

With hydrogenchloride; sodium periodate; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; In methanol; dichloromethane; water;
DOI:10.1021/jo001447t