(2R,4aR,6S,7S,8S,8aR)-6,8-Bis-benzyloxy-7-((4R,5R)-2,2-diethyl-5-hydroxymethyl-[1,3]dioxolan-4-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Base Information

Chemical Name:(2R,4aR,6S,7S,8S,8aR)-6,8-Bis-benzyloxy-7-((4R,5R)-2,2-diethyl-5-hydroxymethyl-[1,3]dioxolan-4-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
CAS No.:162518-32-3
Molecular Formula:C₃₅H₄₂O₉
Molecular Weight:606.713
Hs Code.:

(2R,4aR,6S,7S,8S,8aR)-6,8-Bis-benzyloxy-7-((4R,5R)-2,2-diethyl-5-hydroxymethyl-[1,3]dioxolan-4-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

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Chemical Property of (2R,4aR,6S,7S,8S,8aR)-6,8-Bis-benzyloxy-7-((4R,5R)-2,2-diethyl-5-hydroxymethyl-[1,3]dioxolan-4-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

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Technology Process of (2R,4aR,6S,7S,8S,8aR)-6,8-Bis-benzyloxy-7-((4R,5R)-2,2-diethyl-5-hydroxymethyl-[1,3]dioxolan-4-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

There total 4 articles about (2R,4aR,6S,7S,8S,8aR)-6,8-Bis-benzyloxy-7-((4R,5R)-2,2-diethyl-5-hydroxymethyl-[1,3]dioxolan-4-yl)-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:

: (2R,4aR,6S,7S,8S,8aR)-6,8-Bis-benzyloxy-7-((S)-2,2-diethyl-5-methylene-[1,3]dioxolan-4-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 162518-32-3
(2R,4aR,6S,7S,8S,8aR)-6,8-Bis-benzyloxy-7-((4R,5R)-2,2-diethyl-5-hydroxymethyl-[1,3]dioxolan-4-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: With dimethylsulfide borane complex; In tetrahydrofuran; Yield given; 0 deg C up to RT;
DOI:10.1016/0040-4039(94)02388-R

Reference yield:

: 86833-19-4
benzyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopiranoside

: 162518-32-3
(2R,4aR,6S,7S,8S,8aR)-6,8-Bis-benzyloxy-7-((4R,5R)-2,2-diethyl-5-hydroxymethyl-[1,3]dioxolan-4-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / PCC, 4 Angstroem molecular sieves / CH₂Cl₂ / Ambient temperature

2: 66 percent / LDA / tetrahydrofuran / -78 °C

3: pyridine / tetrahydrofuran / Tebbe methylenation, -40 deg C up to RT

4: BH₃*DMS / tetrahydrofuran / 0 deg C up to RT

With pyridine; dimethylsulfide borane complex; 4 A molecular sieve; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0040-4039(94)02388-R

Reference yield:

: 162601-68-5
(2R,4aR,6S,8S,8aR)-6,8-Bis-benzyloxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one

: 162518-32-3
(2R,4aR,6S,7S,8S,8aR)-6,8-Bis-benzyloxy-7-((4R,5R)-2,2-diethyl-5-hydroxymethyl-[1,3]dioxolan-4-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 66 percent / LDA / tetrahydrofuran / -78 °C

2: pyridine / tetrahydrofuran / Tebbe methylenation, -40 deg C up to RT

3: BH₃*DMS / tetrahydrofuran / 0 deg C up to RT

With pyridine; dimethylsulfide borane complex; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1016/0040-4039(94)02388-R