(3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6S)-spiro<5,5>undec-10-ene

Base Information

Chemical Name:(3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6S)-spiro<5,5>undec-10-ene
CAS No.:92621-59-5
Molecular Formula:C₃₈H₄₀O₆
Molecular Weight:592.732
Hs Code.:

Synonyms:(3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6S)-spiro<5,5>undec-10-ene

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Chemical Property of (3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6S)-spiro<5,5>undec-10-ene

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Technology Process of (3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6S)-spiro<5,5>undec-10-ene

There total 5 articles about (3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6S)-spiro<5,5>undec-10-ene 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: 41.0%

: 92567-59-4,92586-59-9
2,3,4,6-tetra-O-benzyl-1-C-(4-hydroxy-1-Z-butenyl)-D-glucopyranose

: 92567-60-7
(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-2-benzylomethyl-1,7-dioxa-spiro[5.5]undec-10-ene

: 92621-59-5
(3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6S)-spiro<5,5>undec-10-ene

Guidance literature:: With camphor-10-sulfonic acid; In tetrahydrofuran; for 5h; Ambient temperature;
DOI:10.1016/0008-6215(84)85284-2

Reference yield:

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

: 92621-59-5
(3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6S)-spiro<5,5>undec-10-ene

Guidance literature:: Multi-step reaction with 4 steps

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

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

3: 81 percent / hydrogen, pyridine / 5 percent palladium-on-barium sulfate / ethyl acetate / 2 h / Ambient temperature

4: 41 percent / camphorsulfonic acid / tetrahydrofuran / 5 h / Ambient temperature

With pyridine; methanol; n-butyllithium; camphor-10-sulfonic acid; hydrogen; pyridinium p-toluenesulfonate; palladium on barium sulfate; In tetrahydrofuran; ethyl acetate;
DOI:10.1016/0008-6215(84)85284-2

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

: 92621-59-5
(3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6S)-spiro<5,5>undec-10-ene

Guidance literature:: Multi-step reaction with 5 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: 41 percent / camphorsulfonic acid / tetrahydrofuran / 5 h / Ambient temperature

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