(2R,3R,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol

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Chemical Name:(2R,3R,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol
CAS No.:106929-11-7
Molecular Formula:C₄₄H₅₂O₁₀
Molecular Weight:740.891
Hs Code.:

Synonyms:(2R,3R,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol

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Chemical Property of (2R,3R,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol

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Technology Process of (2R,3R,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol

There total 4 articles about (2R,3R,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol 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: 80.0%

: 106929-10-6
(1S,2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-[(Z)-(4R,5S)-4,5-bis-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-2-enyl]-6,8-dioxa-bicyclo[3.2.1]octane

: 106929-11-7
(2R,3R,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol

: (2S,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol

Guidance literature:: With 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; osmium(VIII) oxide; In dichloromethane; at -80 ℃; for 24h; Product distribution; also with achiral diamine, N-methylmorpholine N-oxide (NMMO) / 1,4-diazabicyclo<2,2,2>octane (DABCO) or without diamine; diastereoselectivity;
DOI:10.1021/jo00028a017

Reference yield: 11.0%

: 106929-10-6
(1S,2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-[(Z)-(4R,5S)-4,5-bis-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-2-enyl]-6,8-dioxa-bicyclo[3.2.1]octane

: 106929-11-7
(2R,3R,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol

: 106974-26-9
(2S,3S,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol

Guidance literature:: With pyridine; osmium(VIII) oxide; In tetrahydrofuran; at -40 ℃;
DOI:10.1021/jo00383a045

Reference yield:

: 106929-08-2
[2-((1S,2R,3S,4R,5R)-3,4-Bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-ethyl]-triphenyl-phosphonium; iodide

: 106929-11-7
(2R,3R,4R,5R)-4,5-Bis-benzyloxy-1-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentane-2,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) THF, 0 deg C, 2.) THF, -78 deg C,

2: 60 percent / OsO₄, pyridinium / tetrahydrofuran / -40 °C

With pyridine; osmium(VIII) oxide; n-butyllithium; In tetrahydrofuran;
DOI:10.1021/jo00383a045