(2R,4aR,6S,7S,8S,8aR)-7-Allyl-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Base Information

• Chemical Name: (2R,4aR,6S,7S,8S,8aR)-7-Allyl-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
• CAS No.: 304671-80-5
• Molecular Formula: C₂₄H₂₈O₆
• Molecular Weight: 412.483
• Mol file: 304671-80-5.mol

Synonyms:(2R,4aR,6S,7S,8S,8aR)-7-Allyl-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Chemical Property of (2R,4aR,6S,7S,8S,8aR)-7-Allyl-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,6S,7S,8S,8aR)-7-Allyl-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

There total 2 articles about (2R,4aR,6S,7S,8S,8aR)-7-Allyl-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 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:

methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside (76419-48-2) → (2R,4aR,6S,7S,8S,8aR)-7-Allyl-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (304671-80-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2: diethyl ether; CH₂Cl₂ / -78 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In diethyl ether; dichloromethane; 1: Swern oxidation;

DOI:10.3987/com-00-8987

Reference yield:

methyl 3-O-benzyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose (130983-50-5) + allylmagnesium bromide (1730-25-2) → (2R,4aR,6S,7R,8S,8aR)-7-Allyl-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (304671-79-2) + (2R,4aR,6S,7S,8S,8aR)-7-Allyl-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (304671-80-5)

Guidance literature:

In diethyl ether; dichloromethane; at -78 ℃;

DOI:10.3987/com-00-8987

Reference yield: 97.0%

benzyl bromide (100-39-0) + (2R,4aR,6S,7S,8S,8aR)-7-Allyl-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (304671-80-5) → (2R,4aR,6S,7S,8S,8aR)-7-Allyl-7,8-bis-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (304671-83-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.3987/com-00-8987

upstream raw materials:

methyl 3-O-benzyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose

allylmagnesium bromide

methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

(2R,4aR,6S,7S,8S,8aR)-7-Allyl-7,8-bis-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

((2R,3R,4S,5S,6S)-5-Allyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol

(2S,3S,4S,5S,6S)-3-Allyl-3,4,5-tris-benzyloxy-6-iodomethyl-2-methoxy-tetrahydro-pyran

(2S,3S,4R)-2,3,4-Tris-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5-hydroxy-cyclohexanone