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

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-2-benzylomethyl-1,7-dioxa-spiro[5.5]undec-10-ene
• CAS No.: 92567-60-7
• Molecular Formula: C₃₈H₄₀O₆
• Molecular Weight: 592.732

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

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

Chemical Property:

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

There total 9 articles about (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-2-benzylomethyl-1,7-dioxa-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: 88.0%

3-buten-1-yl (4,5,6,8-tetra-O-benzyl-1,2-dideoxy)-α-D-gluco-oct-1-eno-3-ulopyranoside (213776-91-1) → (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-2-benzylomethyl-1,7-dioxa-spiro[5.5]undec-10-ene (92567-60-7)

Guidance literature:

Grubbs catalyst first generation; In toluene; at 60 ℃; for 16h;

DOI:10.1016/S0040-4039(98)01247-7

Reference yield: 87.0%

(3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6S)-spiro<5,5>undec-10-ene (92621-59-5) → (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-2-benzylomethyl-1,7-dioxa-spiro[5.5]undec-10-ene (92567-60-7)

Guidance literature:

With camphor-10-sulfonic acid; In tetrahydrofuran; at 45 ℃; for 8h;

DOI:10.1016/0008-6215(84)85284-2

Reference yield: 41.0%

2,3,4,6-tetra-O-benzyl-1-C-(4-hydroxy-1-Z-butenyl)-D-glucopyranose (92567-59-4,92586-59-9) → (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-2-benzylomethyl-1,7-dioxa-spiro[5.5]undec-10-ene (92567-60-7) + (3S,4S,5R)-tribenzyloxy-(2R)-benzyloxymethyl-1,7-dioxa-(6S)-spiro<5,5>undec-10-ene (92621-59-5)

Guidance literature:

With camphor-10-sulfonic acid; In tetrahydrofuran; for 5h; Ambient temperature;

DOI:10.1016/0008-6215(84)85284-2

upstream raw materials:

benzyl bromide

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

2,3,4,6-tetra-O-benzyl-1-C-(4-hydroxy-1-Z-butenyl)-D-glucopyranose

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

Downstream raw materials:

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

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