(3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6R)-spiro[5,5]undecane

Base Information

Chemical Name:(3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6R)-spiro[5,5]undecane
CAS No.:92567-61-8
Molecular Formula:C₃₈H₄₂O₆
Molecular Weight:594.748
Hs Code.:

Synonyms:(3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6R)-spiro[5,5]undecane

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Chemical Property of (3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6R)-spiro[5,5]undecane

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Technology Process of (3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6R)-spiro[5,5]undecane

There total 9 articles about (3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6R)-spiro[5,5]undecane 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: 85.0%

: 213776-98-8
(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-2-benzyloxymethyl-1,7-dioxa-spiro[5.5]undec-9-ene

: 92567-61-8
(3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6R)-spiro[5,5]undecane

Guidance literature:: With hydrogen; platinum(IV) oxide; In ethyl acetate;
DOI:10.1016/S0040-4039(98)01247-7

Reference yield:

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 92567-61-8
(3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6R)-spiro[5,5]undecane

Guidance literature:: Multi-step reaction with 4 steps

2: 69 percent / montmorillonite K-10, 4 Angstroem molecular sieves / CH₂Cl₂ / Ambient temperature

3: 82 percent / Grubbs ruthenium catalyst / toluene / 16 h / 60 °C

4: 85 percent / H₂ / PtO₂ / ethyl acetate

With 4 A molecular sieve; montmorillonite K-10; hydrogen; platinum(IV) oxide; Grubbs catalyst first generation; In dichloromethane; ethyl acetate; toluene;
DOI:10.1016/S0040-4039(98)01247-7

Reference yield:

: 4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 92567-61-8
(3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6R)-spiro[5,5]undecane

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / pyridinium chlorochromate, molecular sieves (3A) / CH₂Cl₂ / 0.75 h

2: 1.) 1-butyllithium / 1.) diethyl ether, -15 deg C, 20 min, 2.) ether, -15 deg C, 45 min

3: methanol, pyridinium p-toluenesulfonate / 1 h / Ambient temperature

4: 81 percent / hydrogen, pyridine / 5 percent palladium-on-barium sulfate / ethyl acetate / 2 h / Ambient temperature

5: 56 percent / camphorsulfonic acid / tetrahydrofuran / 5 h / Ambient temperature

6: 76 mg / hydrogen / PtO₂ / ethyl acetate / 0.5 h

With pyridine; methanol; n-butyllithium; 3 A molecular sieve; camphor-10-sulfonic acid; hydrogen; pyridinium p-toluenesulfonate; pyridinium chlorochromate; platinum(IV) oxide; palladium on barium sulfate; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1016/0008-6215(84)85284-2