(2R,3S,4S,5R,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran

Base Information

Chemical Name:(2R,3S,4S,5R,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran
CAS No.:128376-93-2
Molecular Formula:C₂₆H₃₁BrO₅
Molecular Weight:503.433
Hs Code.:

Synonyms:(2R,3S,4S,5R,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran

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Chemical Property of (2R,3S,4S,5R,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran

Chemical Property:

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Technology Process of (2R,3S,4S,5R,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran

There total 1 articles about (2R,3S,4S,5R,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-bromo-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:

: 128376-99-8,128377-31-1
2,3-di-O-allyl-4,6-di-O-benzyl-D-mannopyranosyl p-nitrobenzoate

: 128376-93-2
(2R,3S,4S,5R,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran

Guidance literature:: With hydrogen bromide; In dichloromethane; at -15 ℃; for 0.5h;
DOI:10.1016/0008-6215(90)84167-S

Reference yield: 37.0%

: 67831-42-9
benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

: 128376-93-2
(2R,3S,4S,5R,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran

: 128377-02-6
(1R,2R,3S,4S,5R)-3,4-Bis-allyloxy-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane

: 128377-00-4
benzyl O-(2,3-di-O-allyl-4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

: 128377-01-5
benzyl O-(2,3-di-O-allyl-4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Guidance literature:: With silver silicate; In dichloromethane; at 20 ℃; for 15h; molecular sieve (MS₄A), other solvents : toluene, nitromethane;
DOI:10.1016/0008-6215(90)84167-S

Reference yield:

: 128376-93-2
(2R,3S,4S,5R,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran

: 128377-03-7
benzyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->3)-O-(4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 40 percent / Ag silicate / CH₂Cl₂ / 15 h / 20 °C / molecular sieve (MS₄A), other solvents : toluene, nitromethane

2: 1) 1,4-diazabicyclo<2.2.2>octane (DABCO), 2) HgCl₂, HgO / 1) (Ph₃P)3RhCl / 1) MeCN-EtOH-H₂O (10:5:1), 85 deg C, 45h, 2) acetone-H₂O (10:1), 25 deg C, 4h

3: 40 percent / silver triflate, Bu₄NBr, CuBr₂ / CH₂Cl₂ / 6 h / 25 °C / MS₄A

With 1,4-diaza-bicyclo[2.2.2]octane; silver silicate; tetrabutylammomium bromide; silver trifluoromethanesulfonate; mercury dichloride; mercury(II) oxide; copper(ll) bromide; Wilkinson's catalyst; In dichloromethane;
DOI:10.1016/0008-6215(90)84167-S